# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_jb03-295
_database_code_depnum_ccdc_archive 'CCDC 2243553'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL
Switzerland
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-08-10 downloaded from the CCDC.
;
_audit_creation_date             2023-02-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N O2'
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H15 N O2'
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      orthorhombic
_space_group_IT_number           19
_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                   5.80631(11)
_cell_length_b                   7.77611(12)
_cell_length_c                   31.5189(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1423.09(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7436
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.2260
_cell_measurement_theta_min      2.7760
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.888
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.748
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.75a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0126
0 0 1 0.0060
0 -1 0 0.0611
0 1 0 0.0804
1 0 0 0.0941
-1 0 0 0.0881
1 1 2 0.1007
-1 1 2 0.1039

_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 0.0000 -1.0000 -0.0048 0.0442 0.0205
0.0000 -0.0000 1.0000 0.0048 -0.0442 -0.0205
-0.0000 -1.0000 0.0000 0.0812 -0.0687 0.1670
0.0000 1.0000 -0.0000 -0.0812 0.0687 -0.1670
1.0000 -0.0000 -0.0000 -0.2406 -0.0674 0.0891
-1.0000 0.0000 0.0000 0.2406 0.0674 -0.0891
1.0000 1.0000 2.0000 -0.3124 -0.0869 -0.1189
-1.0000 1.0000 2.0000 0.1689 0.0478 -0.2970

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            12451
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.554
_diffrn_reflns_theta_min         2.804
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -101.00 -72.00   0.50    0.40    --  -67.31   0.00 -60.00   58
  2  ω   -103.00 -77.00   0.50    0.40    --  -69.03   0.00 -30.00   52
  3  ω   -101.00 -75.00   0.50    0.40    --  -67.31   0.00   0.00   52
  4  ω   -100.00 -73.00   0.50    0.40    --  -67.31   0.00  60.00   54
  5  ω   -102.00 -74.00   0.50    0.40    --  -69.03   0.00  90.00   56
  6  ω    -70.00 -43.00   0.50    0.40    --  -74.50  83.00 -41.51   54
  7  ω    -83.00 -28.00   0.50    0.40    --  -67.31 125.00  30.00  110
  8  ω    -55.00 -29.00   0.50    0.40    --  -67.31 125.00 -90.00   52
  9  ω    -86.00 -38.00   0.50    0.40    --  -67.31 125.00-150.00   96
 10  ω     95.00 120.00   0.50    0.40    --   77.95  15.00  60.00   50
 11  ω     80.00 106.00   0.50    0.40    --   77.95  15.00 150.00   52
 12  ω     50.00  76.00   0.50    0.40    --   77.95  15.00 150.00   52
 13  ω     50.00  76.00   0.50    0.40    --   77.95  15.00  60.00   52
 14  ω     48.00  99.00   0.50    0.40    --   78.00   7.00  14.78  102
 15  ω     64.00  95.00   0.50    0.40    --   77.95  15.00 -90.00   62
 16  ω     80.00 106.00   0.50    0.40    --   73.72   0.00-150.00   52
 17  ω     40.00  67.00   0.50    0.40    --   73.72   0.00-180.00   54
 18  ω     61.00  87.00   0.50    0.40    --   78.00-138.00   0.12   52
 19  ω     76.00 101.00   0.50    0.40    --   77.95-125.00 -60.00   50
 20  ω     39.00  98.00   0.50    0.40    --   77.95-125.00-150.00  118
 21  ω     41.00  86.00   0.50    0.40    --   77.95-125.00-180.00   90
 22  ω     40.00  66.00   0.50    0.40    --   77.95-125.00 -60.00   52
 23  ω     59.00  85.00   0.50    0.40    --   77.95-125.00 -30.00   52
 24  ω     40.00  75.00   0.50    0.40    --   77.95-125.00   0.00   70
 25  ω     49.00  97.00   0.50    0.40    --   77.95-125.00 -90.00   96
 26  ω     39.00  65.00   0.50    0.40    --   77.95-125.00  30.00   52
 27  ω     73.00  99.00   0.50    0.40    --   77.95-125.00  30.00   52
 28  ω     74.00  99.00   0.50    0.40    --   77.95-125.00  60.00   50
 29  ω     56.00  81.00   0.50    0.40    --   77.95-125.00 150.00   50
 30  ω     87.00 113.00   0.50    0.40    --   78.00 116.00-139.30   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2406418000
_diffrn_orient_matrix_UB_12      -0.0812452000
_diffrn_orient_matrix_UB_13      0.0047691000
_diffrn_orient_matrix_UB_21      -0.0673658000
_diffrn_orient_matrix_UB_22      0.0687459000
_diffrn_orient_matrix_UB_23      -0.0441520000
_diffrn_orient_matrix_UB_31      0.0890799000
_diffrn_orient_matrix_UB_32      -0.1669656000
_diffrn_orient_matrix_UB_33      -0.0204976000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2786
_reflns_number_total             2932
_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       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_coef       0.0038(6)
_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   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.034
_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)+(0.0451P)²+0.2253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0782
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H) groups
2. Others
 Sof(H18A)=Sof(H18C)=Sof(H18E)=1-FVAR(1)
 Sof(H18B)=Sof(H18D)=Sof(H18F)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16)
3.b Disordered Me refined as rotating group:
 C18(H18A,H18B,H18C,H18D,H18E,H18F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
O1 O 0.9125(3) 0.3908(2) 0.46746(4) 0.0442(4) Uani 1 1 d . . . . .
O2 O 0.6688(2) 0.58727(17) 0.49406(4) 0.0301(3) Uani 1 1 d . . . . .
N1 N 0.5146(3) 0.95979(19) 0.26592(5) 0.0234(3) Uani 1 1 d . . . . .
H1 H 0.572(4) 1.029(3) 0.2449(7) 0.038(6) Uiso 1 1 d . . . . .
C1 C 0.3195(3) 0.8609(2) 0.26266(5) 0.0207(3) Uani 1 1 d . . . . .
C2 C 0.6103(3) 0.9424(2) 0.30510(5) 0.0237(4) Uani 1 1 d . . . . .
H2 H 0.745878 0.998380 0.314794 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4769(3) 0.8299(2) 0.32833(5) 0.0210(3) Uani 1 1 d . . . . .
C4 C 0.2920(3) 0.7788(2) 0.30135(5) 0.0215(3) Uani 1 1 d . . . . .
H4 H 0.171143 0.701885 0.308618 0.026 Uiso 1 1 calc R U . . .
C5 C 0.1889(3) 0.8460(2) 0.22297(5) 0.0212(4) Uani 1 1 d . . . . .
C6 C -0.0249(3) 0.7634(2) 0.22250(5) 0.0239(4) Uani 1 1 d . . . . .
H6 H -0.090653 0.724253 0.248355 0.029 Uiso 1 1 calc R U . . .
C7 C -0.1419(3) 0.7382(2) 0.18467(6) 0.0282(4) Uani 1 1 d . . . . .
H7 H -0.286150 0.680465 0.184738 0.034 Uiso 1 1 calc R U . . .
C8 C -0.0498(3) 0.7966(2) 0.14673(6) 0.0292(4) Uani 1 1 d . . . . .
H8 H -0.130251 0.778556 0.120864 0.035 Uiso 1 1 calc R U . . .
C9 C 0.1606(4) 0.8815(2) 0.14671(6) 0.0298(4) Uani 1 1 d . . . . .
H9 H 0.223679 0.922787 0.120837 0.036 Uiso 1 1 calc R U . . .
C10 C 0.2786(3) 0.9059(2) 0.18454(5) 0.0258(4) Uani 1 1 d . . . . .
H10 H 0.422473 0.964123 0.184309 0.031 Uiso 1 1 calc R U . . .
C11 C 0.5243(3) 0.7715(2) 0.37191(5) 0.0213(3) Uani 1 1 d . . . . .
C12 C 0.7304(3) 0.8144(2) 0.39235(6) 0.0269(4) Uani 1 1 d . . . . .
H12 H 0.838601 0.886208 0.378290 0.032 Uiso 1 1 calc R U . . .
C13 C 0.7797(3) 0.7541(2) 0.43274(6) 0.0284(4) Uani 1 1 d . . . . .
H13 H 0.919338 0.785081 0.446449 0.034 Uiso 1 1 calc R U . . .
C14 C 0.6226(3) 0.6483(2) 0.45271(5) 0.0252(4) Uani 1 1 d . . . . .
C15 C 0.4167(3) 0.6049(2) 0.43406(5) 0.0256(4) Uani 1 1 d . . . . .
H15 H 0.309596 0.533397 0.448490 0.031 Uiso 1 1 calc R U . . .
C16 C 0.3678(3) 0.6674(2) 0.39366(6) 0.0247(4) Uani 1 1 d . . . . .
H16 H 0.225277 0.638791 0.380646 0.030 Uiso 1 1 calc R U . . .
C17 C 0.8208(3) 0.4544(2) 0.49757(6) 0.0283(4) Uani 1 1 d . . . . .
C18 C 0.8469(4) 0.4009(3) 0.54274(6) 0.0358(5) Uani 1 1 d . . . . .
H18A H 0.843211 0.275108 0.544595 0.043 Uiso 0.455(18) 1 calc R U P . .
H18B H 0.720510 0.449121 0.559560 0.043 Uiso 0.545(18) 1 calc R U P . .
H18C H 0.994211 0.443221 0.553758 0.043 Uiso 0.455(18) 1 calc R U P . .
H18D H 0.862077 0.503192 0.560681 0.043 Uiso 0.545(18) 1 calc R U P . .
H18E H 0.984777 0.329179 0.545715 0.043 Uiso 0.455(18) 1 calc R U P . .
H18F H 0.711077 0.335079 0.551517 0.043 Uiso 0.545(18) 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.195(2) . ?
O2 C14 1.413(2) . ?
O2 C17 1.363(2) . ?
N1 H1 0.91(2) . ?
N1 C1 1.372(2) . ?
N1 C2 1.361(2) . ?
C1 C4 1.386(2) . ?
C1 C5 1.468(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(2) . ?
C3 C4 1.426(2) . ?
C3 C11 1.473(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(2) . ?
C5 C10 1.398(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.387(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.400(2) . ?
C11 C16 1.397(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(3) . ?
C14 C15 1.374(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.491(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 H18D 0.9800 . ?
C18 H18E 0.9800 . ?
C18 H18F 0.9800 . ?

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
C17 O2 C14 116.91(13) . . ?
C1 N1 H1 125.1(14) . . ?
C2 N1 H1 124.5(14) . . ?
C2 N1 C1 110.45(14) . . ?
N1 C1 C4 106.71(14) . . ?
N1 C1 C5 122.30(15) . . ?
C4 C1 C5 130.85(15) . . ?
N1 C2 H2 125.8 . . ?
N1 C2 C3 108.39(15) . . ?
C3 C2 H2 125.8 . . ?
C2 C3 C4 106.43(15) . . ?
C2 C3 C11 125.88(16) . . ?
C4 C3 C11 127.66(16) . . ?
C1 C4 C3 108.03(15) . . ?
C1 C4 H4 126.0 . . ?
C3 C4 H4 126.0 . . ?
C6 C5 C1 120.27(15) . . ?
C6 C5 C10 118.35(15) . . ?
C10 C5 C1 121.30(16) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.62(16) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.42(18) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.71(17) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.94(17) . . ?
C10 C9 H9 120.0 . . ?
C5 C10 H10 119.5 . . ?
C9 C10 C5 120.95(17) . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C3 121.03(16) . . ?
C16 C11 C3 120.99(16) . . ?
C16 C11 C12 117.95(16) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.21(17) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 118.96(17) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 O2 119.71(17) . . ?
C15 C14 O2 118.49(16) . . ?
C15 C14 C13 121.75(17) . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.86(17) . . ?
C16 C15 H15 120.6 . . ?
C11 C16 H16 119.4 . . ?
C15 C16 C11 121.23(17) . . ?
C15 C16 H16 119.4 . . ?
O1 C17 O2 122.51(17) . . ?
O1 C17 C18 126.66(19) . . ?
O2 C17 C18 110.80(16) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
C17 C18 H18D 109.5 . . ?
C17 C18 H18E 109.5 . . ?
C17 C18 H18F 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18A C18 H18D 141.1 . . ?
H18A C18 H18E 56.3 . . ?
H18A C18 H18F 56.3 . . ?
H18B C18 H18C 109.5 . . ?
H18B C18 H18D 56.3 . . ?
H18B C18 H18E 141.1 . . ?
H18B C18 H18F 56.3 . . ?
H18C C18 H18D 56.3 . . ?
H18C C18 H18E 56.3 . . ?
H18C C18 H18F 141.1 . . ?
H18D C18 H18E 109.5 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C13 H13 O2 0.95 2.57 3.457(2) 155.7 4_566 yes
C15 H15 O1 0.95 2.63 3.528(3) 158.5 1_455 yes
C18 H18F O1 0.98 2.54 3.407(3) 147.6 4_456 yes

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
O2 C14 C15 C16 178.70(15) . . . . ?
N1 C1 C4 C3 -0.24(18) . . . . ?
N1 C1 C5 C6 -171.26(15) . . . . ?
N1 C1 C5 C10 11.9(2) . . . . ?
N1 C2 C3 C4 -0.25(19) . . . . ?
N1 C2 C3 C11 177.90(16) . . . . ?
C1 N1 C2 C3 0.1(2) . . . . ?
C1 C5 C6 C7 -175.46(16) . . . . ?
C1 C5 C10 C9 175.83(16) . . . . ?
C2 N1 C1 C4 0.09(19) . . . . ?
C2 N1 C1 C5 -176.02(15) . . . . ?
C2 C3 C4 C1 0.31(19) . . . . ?
C2 C3 C11 C12 -6.9(3) . . . . ?
C2 C3 C11 C16 174.95(17) . . . . ?
C3 C11 C12 C13 -177.44(16) . . . . ?
C3 C11 C16 C15 176.81(16) . . . . ?
C4 C1 C5 C6 13.7(3) . . . . ?
C4 C1 C5 C10 -163.20(17) . . . . ?
C4 C3 C11 C12 170.87(17) . . . . ?
C4 C3 C11 C16 -7.3(3) . . . . ?
C5 C1 C4 C3 175.41(16) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C6 C5 C10 C9 -1.1(3) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C5 0.0(3) . . . . ?
C10 C5 C6 C7 1.5(2) . . . . ?
C11 C3 C4 C1 -177.80(16) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C11 C16 C15 -1.4(2) . . . . ?
C12 C13 C14 O2 -179.28(16) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 O2 C17 O1 0.0(3) . . . . ?
C14 O2 C17 C18 -178.37(16) . . . . ?
C14 C15 C16 C11 0.5(3) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?
C17 O2 C14 C13 -77.8(2) . . . . ?
C17 O2 C14 C15 104.46(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.506
_oxdiff_exptl_absorpt_empirical_full_min 0.738
####################################################################### 
# 
# 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_jb03-227
_database_code_depnum_ccdc_archive 'CCDC 2264031'
loop_
_audit_author_name
_audit_author_address
'Rosario Scopelliti'
;Ecole polytechnique federale de lausanne
Switzerland
;
_audit_update_record             
;
2023-05-19 deposited with the CCDC.	2023-08-10 downloaded from the CCDC.
;
_audit_creation_date             2022-10-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
N-(4-(1-Azido-4-phenylbut-3-yn-2-yl)phenyl)acetamide
_chemical_formula_moiety         'C18 H16 N4 O'
_chemical_formula_sum            'C18 H16 N4 O'
_chemical_formula_weight         304.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H16 N4 O1'
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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   43.729(2)
_cell_length_b                   9.4992(4)
_cell_length_c                   7.5184(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3123.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3508
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      70.4070
_cell_measurement_theta_min      4.0300
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.855
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 0 0.0961
2 0 -1 0.0885
-2 0 1 0.0868
1 2 0 0.1353
1 -2 -1 0.1055
-1 2 1 0.1263
1 1 0 0.1315
1 -1 -1 0.1024
-2 -1 0 0.0915
1 2 2 0.1101
-1 1 2 0.1028
-1 0 0 0.0346
1 0 0 0.0322
27 1 -1 0.0400
7 -3 4 0.1126
-26 1 -2 0.0790
23 2 2 0.0628
14 0 4 0.0934
-10 0 -5 0.0964
-21 -2 -3 0.0867
-23 -3 0 0.0653
26 2 1 0.0396
-25 -3 1 0.0547
27 2 0 0.0313
-27 0 1 0.0350
-28 0 0 0.0371

_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.067
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0005 -0.9998 0.0005 -0.1462 0.0421 -0.0662
2.0013 -0.0008 -0.9999 -0.1076 -0.0212 0.1868
-2.0013 0.0008 0.9999 0.1076 0.0212 -0.1868
0.9986 1.9998 -0.0005 0.2760 0.0118 0.1737
1.0027 -2.0007 -0.9994 -0.3836 -0.0330 0.0131
-1.0027 2.0007 0.9994 0.3836 0.0330 -0.0131
0.9992 1.0000 -0.0002 0.1353 0.0219 0.0937
1.0021 -1.0008 -0.9997 -0.2429 -0.0431 0.0931
-1.9991 -1.0001 0.0001 -0.1298 -0.0538 -0.1075
0.9953 2.0020 1.9998 0.4693 0.1821 -0.1448
-1.0037 1.0019 1.9998 0.3395 0.1282 -0.2523
-0.9999 -0.0001 -0.0001 0.0055 -0.0320 -0.0138
0.9999 0.0001 0.0001 -0.0055 0.0320 0.0138
27.0332 0.9375 -1.2824 -0.1409 0.7454 0.6516
7.2107 -3.2213 3.9742 -0.1100 0.6014 -0.7913
-26.0243 1.3865 -1.6116 0.1834 -0.9830 0.0091
22.8210 2.4110 2.1864 0.4244 0.8914 0.1588
13.9828 0.3490 4.2413 0.3811 0.8047 -0.4552
-9.9752 0.3492 -4.5637 -0.3360 -0.7111 0.6176
-20.9494 -1.8454 -2.9531 -0.4291 -0.9026 0.0344
-23.2357 -3.4917 0.4403 -0.3209 -0.6701 -0.6693
26.4206 2.1139 0.6065 0.2103 0.8749 0.4363
-25.3193 -2.6685 0.6176 -0.1764 -0.7298 -0.6605
26.9270 1.9341 -0.1437 0.1098 0.8290 0.5484
-27.4176 -0.3097 1.2325 0.2266 -0.7682 -0.5988
-28.2069 0.4590 0.3936 0.2583 -0.8726 -0.4145

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11322
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.799
_diffrn_reflns_theta_min         4.044
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -73.00   0.50    2.32    --  -67.15   0.00  90.00   62
  2  ω   -102.00 -76.00   0.50    2.32    --  -69.26   0.00 150.00   52
  3  ω    -98.00 -73.00   0.50    2.32    --  -69.26   0.00  30.00   50
  4  ω   -102.00 -72.00   0.50    2.32    --  -67.15   0.00 -60.00   60
  5  ω   -103.00 -73.00   0.50    2.32    --  -67.15   0.00-120.00   60
  6  ω     40.00  75.00   0.50    2.32    --   78.01 -95.00 -90.00   70
  7  ω     34.00  78.00   0.50    2.32    --   69.47 -95.00-150.00   88
  8  ω     28.00  53.00   0.50    2.32    --   66.10 -95.00-180.00   50
  9  ω     28.00  53.00   0.50    2.32    --   66.10 -95.00  30.00   50
 10  ω     34.00  60.00   0.50    2.32    --   69.47-125.00 150.00   52
 11  ω     68.00  94.00   0.50    2.32    --   69.47-125.00 150.00   52
 12  ω     57.00  85.00   0.50    2.32    --   78.01 -95.00 150.00   56
 13  ω     49.00 107.00   0.50    2.32    --   78.01  15.00 120.00  116
 14  ω     84.00 110.00   0.50    2.32    --   78.01  15.00  30.00   52
 15  ω     49.00  74.00   0.50    2.32    --   78.01  15.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0055194000
_diffrn_orient_matrix_UB_12      0.1407976000
_diffrn_orient_matrix_UB_13      0.0964596000
_diffrn_orient_matrix_UB_21      0.0319615000
_diffrn_orient_matrix_UB_22      -0.0100438000
_diffrn_orient_matrix_UB_23      0.0851931000
_diffrn_orient_matrix_UB_31      0.0137741000
_diffrn_orient_matrix_UB_32      0.0799470000
_diffrn_orient_matrix_UB_33      -0.1593125000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2117
_reflns_number_total             3060
_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       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     122
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0691P)²+1.1968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1460
_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. Restrained distances
 C3-C1 \\sim C2-C1
 with sigma of 0.01
 N5-N4 \\sim N6-N5 \\sim N2-N1 \\sim N3-N2
 with sigma of 0.02
 N1-C2 \\sim N4-C3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N1 \\sim N2 \\sim N3 \\sim N4 \\sim N5 \\sim N6 \\sim C1 \\sim C2 \\sim C3:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(N4)=Sof(N5)=Sof(N6)=Sof(H1B)=Sof(C3)=Sof(H3A)=Sof(H3B)=1-FVAR(1)
 Sof(N1)=Sof(N2)=Sof(N3)=Sof(H1A)=Sof(C2)=Sof(H2A)=Sof(H2B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1A), C1(H1B)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
5.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
O1 O 0.50853(3) 0.23508(15) 0.3436(2) 0.0363(4) Uani 1 1 d . . . . .
N1 N 0.37306(7) 0.4605(3) 0.8318(4) 0.0475(9) Uani 0.736(4) 1 d D U P A 1
N2 N 0.37979(7) 0.5685(4) 0.9106(5) 0.0445(8) Uani 0.736(4) 1 d D U P A 1
N3 N 0.3873(3) 0.6609(10) 0.9977(10) 0.0621(16) Uani 0.736(4) 1 d D U P A 1
N4 N 0.3597(2) 0.5699(10) 0.6992(12) 0.0511(19) Uani 0.264(4) 1 d D U P A 2
N5 N 0.3719(2) 0.6172(11) 0.8273(14) 0.0515(19) Uani 0.264(4) 1 d D U P A 2
N6 N 0.3839(8) 0.670(3) 0.947(3) 0.067(5) Uani 0.264(4) 1 d D U P A 2
N7 N 0.48687(4) 0.44901(19) 0.2952(2) 0.0288(4) Uani 1 1 d . . . . .
H7 H 0.4893(5) 0.531(3) 0.256(3) 0.037(7) Uiso 1 1 d . . . . .
C1 C 0.36289(5) 0.3727(3) 0.5252(3) 0.0403(6) Uani 1 1 d D U . . .
H1A H 0.359676 0.275063 0.571164 0.048 Uiso 0.736(4) 1 calc R U P A 1
H1B H 0.361535 0.267862 0.533483 0.048 Uiso 0.264(4) 1 calc R U P A 2
C2 C 0.35377(9) 0.4827(5) 0.6712(5) 0.0448(10) Uani 0.736(4) 1 d D U P A 1
H2A H 0.356806 0.579338 0.625151 0.054 Uiso 0.736(4) 1 calc R U P A 1
H2B H 0.331912 0.471347 0.702391 0.054 Uiso 0.736(4) 1 calc R U P A 1
C3 C 0.3557(3) 0.4149(12) 0.7153(11) 0.049(2) Uani 0.264(4) 1 d D U P A 2
H3A H 0.334545 0.389355 0.749443 0.059 Uiso 0.264(4) 1 calc R U P A 2
H3B H 0.370300 0.373136 0.800970 0.059 Uiso 0.264(4) 1 calc R U P A 2
C4 C 0.39603(5) 0.3918(2) 0.4684(3) 0.0334(5) Uani 1 1 d . . . . .
C5 C 0.40462(5) 0.5047(2) 0.3621(3) 0.0348(5) Uani 1 1 d . . . . .
H5 H 0.389651 0.571453 0.326341 0.042 Uiso 1 1 calc R U . . .
C6 C 0.43453(5) 0.5216(2) 0.3075(3) 0.0318(5) Uani 1 1 d . . . . .
H6 H 0.439903 0.599594 0.234910 0.038 Uiso 1 1 calc R U . . .
C7 C 0.45687(5) 0.4253(2) 0.3580(3) 0.0274(5) Uani 1 1 d . . . . .
C8 C 0.44869(5) 0.3132(2) 0.4687(3) 0.0304(5) Uani 1 1 d . . . . .
H8 H 0.463701 0.247964 0.507971 0.037 Uiso 1 1 calc R U . . .
C9 C 0.41847(5) 0.2982(2) 0.5205(3) 0.0328(5) Uani 1 1 d . . . . .
H9 H 0.413003 0.221031 0.594259 0.039 Uiso 1 1 calc R U . . .
C10 C 0.51037(5) 0.3570(2) 0.2882(3) 0.0290(5) Uani 1 1 d . . . . .
C11 C 0.53936(5) 0.4126(2) 0.2090(3) 0.0360(5) Uani 1 1 d . . . . .
H11A H 0.556052 0.402255 0.294985 0.054 Uiso 1 1 calc R U . . .
H11B H 0.536753 0.512342 0.179394 0.054 Uiso 1 1 calc R U . . .
H11C H 0.544244 0.359603 0.100856 0.054 Uiso 1 1 calc R U . . .
C12 C 0.34162(5) 0.4012(3) 0.3784(3) 0.0389(6) Uani 1 1 d . . . . .
C13 C 0.32544(5) 0.4334(3) 0.2570(3) 0.0401(6) Uani 1 1 d . . . . .
C14 C 0.30670(5) 0.4783(3) 0.1102(3) 0.0368(5) Uani 1 1 d . . . . .
C15 C 0.28813(6) 0.3847(3) 0.0179(3) 0.0442(6) Uani 1 1 d . . . . .
H15 H 0.287690 0.288107 0.050384 0.053 Uiso 1 1 calc R U . . .
C16 C 0.27018(6) 0.4330(3) -0.1225(3) 0.0506(7) Uani 1 1 d . . . . .
H16 H 0.257625 0.368729 -0.186127 0.061 Uiso 1 1 calc R U . . .
C17 C 0.27049(6) 0.5726(3) -0.1697(4) 0.0533(7) Uani 1 1 d . . . . .
H17 H 0.258126 0.604808 -0.265281 0.064 Uiso 1 1 calc R U . . .
C18 C 0.28884(6) 0.6665(3) -0.0777(4) 0.0505(7) Uani 1 1 d . . . . .
H18 H 0.288940 0.763327 -0.109477 0.061 Uiso 1 1 calc R U . . .
C19 C 0.30692(6) 0.6196(3) 0.0598(3) 0.0432(6) Uani 1 1 d . . . . .
H19 H 0.319725 0.684229 0.121069 0.052 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.233(2) . ?
N1 N2 1.221(4) . ?
N1 C2 1.488(4) . ?
N2 N3 1.142(8) . ?
N4 N5 1.188(11) . ?
N4 C3 1.488(12) . ?
N5 N6 1.157(14) . ?
N7 H7 0.84(3) . ?
N7 C7 1.412(3) . ?
N7 C10 1.350(3) . ?
C1 H1A 1.0000 . ?
C1 H1B 1.0000 . ?
C1 C2 1.566(4) . ?
C1 C3 1.517(8) . ?
C1 C4 1.522(3) . ?
C1 C12 1.468(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.390(3) . ?
C4 C9 1.381(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(3) . ?
C7 C8 1.398(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.497(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.195(3) . ?
C13 C14 1.439(3) . ?
C14 C15 1.390(3) . ?
C14 C19 1.395(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.393(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.374(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.375(4) . ?
C19 H19 0.9500 . ?

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 C2 114.3(3) . . ?
N3 N2 N1 172.9(6) . . ?
N5 N4 C3 111.1(9) . . ?
N6 N5 N4 176.4(18) . . ?
C7 N7 H7 112.4(15) . . ?
C10 N7 H7 119.4(15) . . ?
C10 N7 C7 128.10(19) . . ?
C2 C1 H1A 109.9 . . ?
C3 C1 H1B 101.1 . . ?
C3 C1 C4 115.5(5) . . ?
C4 C1 H1A 109.9 . . ?
C4 C1 H1B 101.1 . . ?
C4 C1 C2 111.1(2) . . ?
C12 C1 H1A 109.9 . . ?
C12 C1 H1B 101.1 . . ?
C12 C1 C2 104.0(2) . . ?
C12 C1 C3 121.9(5) . . ?
C12 C1 C4 111.74(19) . . ?
N1 C2 C1 109.2(3) . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
N4 C3 C1 99.2(7) . . ?
N4 C3 H3A 111.9 . . ?
N4 C3 H3B 111.9 . . ?
C1 C3 H3A 111.9 . . ?
C1 C3 H3B 111.9 . . ?
H3A C3 H3B 109.6 . . ?
C5 C4 C1 120.7(2) . . ?
C9 C4 C1 121.4(2) . . ?
C9 C4 C5 117.9(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 N7 117.16(19) . . ?
C6 C7 C8 118.9(2) . . ?
C8 C7 N7 123.92(19) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 H8 120.3 . . ?
C4 C9 C8 122.2(2) . . ?
C4 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
O1 C10 N7 123.0(2) . . ?
O1 C10 C11 121.41(19) . . ?
N7 C10 C11 115.57(19) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C1 175.2(3) . . ?
C12 C13 C14 177.3(3) . . ?
C15 C14 C13 121.7(2) . . ?
C15 C14 C19 118.9(2) . . ?
C19 C14 C13 119.4(2) . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 119.9(3) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.8(2) . . ?
C18 C19 H19 119.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N7 H7 O1 0.84(3) 2.08(3) 2.918(2) 175(2) 3_655 yes

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 C2 C1 144.8(3) . . . . ?
N5 N4 C3 C1 -140.7(9) . . . . ?
N7 C7 C8 C9 -178.95(19) . . . . ?
C1 C4 C5 C6 -179.0(2) . . . . ?
C1 C4 C9 C8 179.4(2) . . . . ?
C2 C1 C4 C5 -73.6(3) . . . . ?
C2 C1 C4 C9 106.3(3) . . . . ?
C3 C1 C4 C5 -103.0(5) . . . . ?
C3 C1 C4 C9 76.9(6) . . . . ?
C4 C1 C2 N1 -62.0(4) . . . . ?
C4 C1 C3 N4 68.8(9) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C4 C9 C8 -0.7(3) . . . . ?
C5 C6 C7 N7 179.31(19) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
C6 C7 C8 C9 2.0(3) . . . . ?
C7 N7 C10 O1 -2.2(3) . . . . ?
C7 N7 C10 C11 178.25(19) . . . . ?
C7 C8 C9 C4 -0.9(3) . . . . ?
C9 C4 C5 C6 1.1(3) . . . . ?
C10 N7 C7 C6 -162.5(2) . . . . ?
C10 N7 C7 C8 18.5(3) . . . . ?
C12 C1 C2 N1 177.6(3) . . . . ?
C12 C1 C3 N4 -72.4(9) . . . . ?
C12 C1 C4 C5 42.1(3) . . . . ?
C12 C1 C4 C9 -138.0(2) . . . . ?
C13 C14 C15 C16 179.5(2) . . . . ?
C13 C14 C19 C18 -178.7(2) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?
C15 C14 C19 C18 0.8(4) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C17 C18 C19 C14 -1.1(4) . . . . ?
C19 C14 C15 C16 0.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.988
_oxdiff_exptl_absorpt_empirical_full_min 0.536
_exptl_crystal_recrystallization_method 'Slow evaporation'
