# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_mjp_1
_database_code_depnum_ccdc_archive 'CCDC 1896805'
loop_
_audit_author_name
_audit_author_address
'Milosz Pawlicki'
;Department of Chemistry University of Wroclaw
Poland
;
_audit_update_record             
;
2019-02-12 deposited with the CCDC.	2019-04-25 downloaded from the CCDC.
;
_audit_creation_date             2019-01-19
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N3'
_chemical_formula_sum            'C15 H13 N3'
_chemical_formula_weight         235.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H12 N3'
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'

_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                   5.4882(7)
_cell_length_b                   11.1825(15)
_cell_length_c                   11.6413(16)
_cell_angle_alpha                62.292(14)
_cell_angle_beta                 80.059(11)
_cell_angle_gamma                76.727(11)
_cell_volume                     613.82(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    833
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.1420
_cell_measurement_theta_min      4.3023
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.2778
_exptl_crystal_size_mid          0.1528
_exptl_crystal_size_min          0.0855
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3681
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.939
_diffrn_reflns_theta_min         4.302
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.1956
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -105.00  -21.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.7393  -37.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega  -71.00   27.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.7393   37.0000    0.0000 98

#__ type_ start__ end____ width___ exp.time_
  3 omega    5.00   97.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7393 -125.0000 -180.0000 92

#__ type_ start__ end____ width___ exp.time_
  4 omega   87.00  119.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7393  125.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega -109.00  -83.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      -93.0000  125.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   96.00  171.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513   45.0000   90.0000 75

#__ type_ start__ end____ width___ exp.time_
  7 omega   44.00   77.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  -45.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
  8 omega   64.00  148.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513   15.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00   70.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  -45.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   35.00  143.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  -77.0000  -60.0000 108

#__ type_ start__ end____ width___ exp.time_
 11 omega   37.00   75.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  -45.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
 12 omega   76.00  138.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  125.0000    0.0000 62

#__ type_ start__ end____ width___ exp.time_
 13 omega  147.00  176.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  125.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega   42.00   68.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513 -137.0000 -165.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   45.00   70.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  -45.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   77.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  -45.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
 17 omega   90.00  116.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  125.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega  148.00  177.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  125.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
 19 omega   37.00   62.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  -45.0000 -150.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0782583000
_diffrn_orient_matrix_UB_12      -0.1475274000
_diffrn_orient_matrix_UB_13      0.1043833000
_diffrn_orient_matrix_UB_21      0.1124481000
_diffrn_orient_matrix_UB_22      -0.0447315000
_diffrn_orient_matrix_UB_23      -0.1075767000
_diffrn_orient_matrix_UB_31      0.2547556000
_diffrn_orient_matrix_UB_32      0.0343570000
_diffrn_orient_matrix_UB_33      0.0024017000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1644
_reflns_number_total             2349
_reflns_odcompleteness_completeness 96.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0956
_refine_ls_restrained_S_all      1.009
_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)+(0.1636P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2368
_refine_ls_wR_factor_ref         0.2677
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H001(0.039) H003(0.045) H007(0.042) H008(0.039) H009(0.04)
 H00A(0.04) H00B(0.042) H00C(0.045) H00D(0.047) H00E(0.045) H00G(0.046)
 H00H(0.043) H00I(0.048)
 Fixed X: H001(1.032603) H003(0.428675) H007(0.818204) H008(0.776617)
 H009(1.145227) H00A(0.431004) H00B(1.196104) H00C(0.469315) H00D(0.335039)
 H00E(0.640448) H00G(0.247112) H00H(1.046224) H00I(1.065088)
 Fixed Y: H001(0.353793) H003(0.219224) H007(0.076273) H008(0.442068)
 H009(0.597311) H00A(0.648091) H00B(0.13653) H00C(0.338076) H00D(0.842314)
 H00E(0.91631) H00G(0.20364) H00H(0.79046) H00I(-0.041705)
 Fixed Z: H001(0.586699) H003(0.452648) H007(0.528152) H008(0.122538)
 H009(0.144797) H00A(0.291756) H00B(0.758197) H00C(0.076382) H00D(0.102509)
 H00E(-0.068395) H00G(0.284979) H00H(-0.0458) H00I(0.724903)
;
_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
N001 N 1.0118(5) 0.2759(3) 0.5958(3) 0.0329(6) Uani 1 1 d . . . . .
H001 H 1.032603 0.353793 0.586699 0.039 Uiso 1 1 calc R . . . .
N002 N 0.8681(5) 0.4872(3) 0.3573(2) 0.0319(6) Uani 1 1 d . . . . .
N003 N 0.4726(5) 0.2600(3) 0.3709(3) 0.0377(7) Uani 1 1 d . . . . .
H003 H 0.428675 0.219224 0.452648 0.045 Uiso 1 1 calc R . . . .
C004 C 0.7976(5) 0.3716(3) 0.3940(3) 0.0298(7) Uani 1 1 d . . . . .
C005 C 0.7970(6) 0.6020(3) 0.2382(3) 0.0316(7) Uani 1 1 d . . . . .
C006 C 0.8821(6) 0.2577(3) 0.5152(3) 0.0302(7) Uani 1 1 d . . . . .
C007 C 0.8907(6) 0.1186(3) 0.5628(3) 0.0353(7) Uani 1 1 d . . . . .
H007 H 0.818204 0.076273 0.528152 0.042 Uiso 1 1 calc R . . . .
C008 C 0.6692(6) 0.3853(3) 0.1838(3) 0.0326(7) Uani 1 1 d . . . . .
H008 H 0.776617 0.442068 0.122538 0.039 Uiso 1 1 calc R . . . .
C009 C 0.9822(6) 0.6462(3) 0.1360(3) 0.0332(7) Uani 1 1 d . . . . .
H009 H 1.145227 0.597311 0.144797 0.040 Uiso 1 1 calc R . . . .
C00A C 0.5549(6) 0.6768(3) 0.2242(3) 0.0337(7) Uani 1 1 d . . . . .
H00A H 0.431004 0.648091 0.291756 0.040 Uiso 1 1 calc R . . . .
C00B C 1.1022(6) 0.1516(3) 0.6920(3) 0.0351(7) Uani 1 1 d . . . . .
H00B H 1.196104 0.136530 0.758197 0.042 Uiso 1 1 calc R . . . .
C00C C 0.4958(6) 0.3271(4) 0.1577(3) 0.0379(8) Uani 1 1 d . . . . .
H00C H 0.469315 0.338076 0.076382 0.045 Uiso 1 1 calc R . . . .
C00D C 0.4977(6) 0.7929(3) 0.1108(4) 0.0388(8) Uani 1 1 d . . . . .
H00D H 0.335039 0.842314 0.102509 0.047 Uiso 1 1 calc R . . . .
C00E C 0.6800(7) 0.8376(3) 0.0081(3) 0.0375(8) Uani 1 1 d . . . . .
H00E H 0.640448 0.916310 -0.068395 0.045 Uiso 1 1 calc R . . . .
C00F C 0.6513(6) 0.3431(3) 0.3170(3) 0.0301(7) Uani 1 1 d . . . . .
C00G C 0.3738(6) 0.2518(4) 0.2736(4) 0.0382(8) Uani 1 1 d . . . . .
H00G H 0.247112 0.203640 0.284979 0.046 Uiso 1 1 calc R . . . .
C00H C 0.9230(6) 0.7622(3) 0.0222(3) 0.0360(7) Uani 1 1 d . . . . .
H00H H 1.046224 0.790460 -0.045800 0.043 Uiso 1 1 calc R . . . .
C00I C 1.0292(7) 0.0524(4) 0.6734(3) 0.0404(8) Uani 1 1 d . . . . .
H00I H 1.065088 -0.041705 0.724903 0.048 Uiso 1 1 calc R . . . .


_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
N001 H001 0.8600 . ?
N001 C006 1.379(4) . ?
N001 C00B 1.364(4) . ?
N002 C004 1.290(4) . ?
N002 C005 1.423(4) . ?
N003 H003 0.8600 . ?
N003 C00F 1.372(4) . ?
N003 C00G 1.385(4) . ?
C004 C006 1.453(4) . ?
C004 C00F 1.477(4) . ?
C005 C009 1.400(4) . ?
C005 C00A 1.389(4) . ?
C006 C007 1.380(5) . ?
C007 H007 0.9300 . ?
C007 C00I 1.405(4) . ?
C008 H008 0.9300 . ?
C008 C00C 1.410(5) . ?
C008 C00F 1.387(4) . ?
C009 H009 0.9300 . ?
C009 C00H 1.378(5) . ?
C00A H00A 0.9300 . ?
C00A C00D 1.375(5) . ?
C00B H00B 0.9300 . ?
C00B C00I 1.376(5) . ?
C00C H00C 0.9300 . ?
C00C C00G 1.366(5) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.393(5) . ?
C00E H00E 0.9300 . ?
C00E C00H 1.396(5) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?

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
C006 N001 H001 125.1 . . ?
C00B N001 H001 125.1 . . ?
C00B N001 C006 109.7(3) . . ?
C004 N002 C005 121.1(3) . . ?
C00F N003 H003 125.2 . . ?
C00F N003 C00G 109.6(3) . . ?
C00G N003 H003 125.2 . . ?
N002 C004 C006 118.2(3) . . ?
N002 C004 C00F 124.6(3) . . ?
C006 C004 C00F 117.0(3) . . ?
C009 C005 N002 118.5(3) . . ?
C00A C005 N002 121.9(3) . . ?
C00A C005 C009 119.4(3) . . ?
N001 C006 C004 121.1(3) . . ?
N001 C006 C007 107.3(3) . . ?
C007 C006 C004 131.0(3) . . ?
C006 C007 H007 126.3 . . ?
C006 C007 C00I 107.5(3) . . ?
C00I C007 H007 126.3 . . ?
C00C C008 H008 126.0 . . ?
C00F C008 H008 126.0 . . ?
C00F C008 C00C 108.0(3) . . ?
C005 C009 H009 120.0 . . ?
C00H C009 C005 120.0(3) . . ?
C00H C009 H009 120.0 . . ?
C005 C00A H00A 119.9 . . ?
C00D C00A C005 120.3(3) . . ?
C00D C00A H00A 119.9 . . ?
N001 C00B H00B 126.2 . . ?
N001 C00B C00I 107.6(3) . . ?
C00I C00B H00B 126.2 . . ?
C008 C00C H00C 126.2 . . ?
C00G C00C C008 107.7(3) . . ?
C00G C00C H00C 126.2 . . ?
C00A C00D H00D 119.6 . . ?
C00A C00D C00E 120.9(3) . . ?
C00E C00D H00D 119.6 . . ?
C00D C00E H00E 120.6 . . ?
C00D C00E C00H 118.8(3) . . ?
C00H C00E H00E 120.6 . . ?
N003 C00F C004 123.7(3) . . ?
N003 C00F C008 106.9(3) . . ?
C008 C00F C004 129.3(3) . . ?
N003 C00G H00G 126.1 . . ?
C00C C00G N003 107.8(3) . . ?
C00C C00G H00G 126.1 . . ?
C009 C00H C00E 120.7(3) . . ?
C009 C00H H00H 119.7 . . ?
C00E C00H H00H 119.7 . . ?
C007 C00I H00I 126.0 . . ?
C00B C00I C007 107.9(3) . . ?
C00B C00I H00I 126.0 . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_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
3 0 -3 0.1045 2.8574 0.1310 -3.3347 -0.1438 0.6742 0.7244
0 3 7 0.0747 -0.4860 3.3600 7.1728 0.2150 -0.9766 0.0089
0 -3 5 0.0583 0.0214 -2.7341 4.8718 0.9136 -0.3994 -0.0768
1 5 -2 0.0420 0.5543 5.0222 -2.3868 -0.9467 0.0944 0.3080
-1 -5 2 0.0558 -0.8123 -5.1510 2.1511 0.9209 -0.0923 -0.3787
1 6 0 0.0379 0.6581 6.3636 -0.1353 -0.9014 -0.1961 0.3860
0 -6 1 0.0420 0.2066 -5.9317 0.7146 0.9658 0.2117 -0.1495
0 -6 0 0.0452 -0.2863 -6.2231 0.3887 0.9362 0.2044 -0.2858
0 7 2 0.0420 0.2496 6.9867 1.8185 -0.8214 -0.4801 0.3080
0 -7 -2 0.0488 -0.2114 -6.9725 -1.8004 0.8242 0.4818 -0.2977
0 7 4 0.0536 0.4190 7.1927 3.9122 -0.6200 -0.6955 0.3633
0 5 7 0.0677 -0.0588 5.4164 6.7730 -0.0967 -0.9775 0.1874
0 -6 -7 0.0766 -0.3301 -5.6523 -6.8339 0.0947 0.9509 -0.2947
1 2 7 0.0714 0.7571 2.4098 7.4605 0.4825 -0.8252 0.2936
0 -2 -7 0.0740 -0.2475 -1.9611 -7.3754 -0.4999 0.8533 -0.1481
3 2 4 0.1314 3.1659 1.8260 4.3617 0.4337 -0.1949 0.8797
0 3 -5 0.0598 -0.2557 2.5156 -5.0324 -0.9164 0.4001 0.0092
-1 -4 3 0.0705 -1.3123 -3.7684 3.4843 0.8169 -0.3538 -0.4554
1 -4 3 0.0498 0.5034 -4.2239 3.1871 0.9952 -0.0973 -0.0092
0 5 -3 0.0440 0.1569 4.7850 -2.7020 -0.9757 0.0943 0.1979
0 6 0 0.0411 0.1592 6.1700 -0.4516 -0.9449 -0.2095 0.2515
-3 -3 -2 0.1179 -3.4517 -3.3530 -2.2495 -0.0103 0.0038 -0.9999
1 -6 1 0.0465 0.5752 -5.6378 0.9469 0.9756 0.2150 -0.0449
0 -7 -2 0.0453 0.3077 -6.7028 -1.5472 0.8514 0.5009 -0.1556
2 -5 -2 0.0833 2.1697 -4.5722 -2.2172 0.6129 0.6870 0.3903
0 7 4 0.0557 -0.2310 6.9206 3.7168 -0.6511 -0.7354 0.1878
2 -4 -3 0.0929 2.3834 -3.6131 -3.4936 0.3549 0.8055 0.4747
-1 5 6 0.0764 -0.6861 4.8940 6.4990 -0.0973 -0.9952 0.0090

_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_mf001
_database_code_depnum_ccdc_archive 'CCDC 1896807'
loop_
_audit_author_name
_audit_author_address
'Milosz Pawlicki'
;Department of Chemistry University of Wroclaw
Poland
;
_audit_update_record             
;
2019-02-12 deposited with the CCDC.	2019-04-25 downloaded from the CCDC.
;
_audit_creation_date             2018-12-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N3 O2'
_chemical_formula_sum            'C17 H17 N3 O2'
_chemical_formula_weight         295.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H17 N3 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.1050(5)
_cell_length_b                   12.8664(4)
_cell_length_c                   15.5822(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.952(3)
_cell_angle_gamma                90
_cell_volume                     3026.60(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4273
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35.0780
_cell_measurement_theta_min      3.2870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.1606
_exptl_crystal_size_min          0.1381
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.610
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12949
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.610
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.877
_diffrn_reflns_theta_min         3.167
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.3359
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.610
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -54.00   60.75   0.7500   50.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -79.0000    0.0000 153

#__ type_ start__ end____ width___ exp.time_
  2 omega  -54.00   60.75   0.7500   50.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -79.0000   90.0000 153

#__ type_ start__ end____ width___ exp.time_
  3 omega  -54.00   60.75   0.7500   50.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -79.0000  180.0000 153

#__ type_ start__ end____ width___ exp.time_
  4 omega  -54.00   60.75   0.7500   50.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -79.0000  270.0000 153

#__ type_ start__ end____ width___ exp.time_
  5 omega  -54.00    7.50   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000  -79.0000   45.0000 82
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0392346000
_diffrn_orient_matrix_UB_12      -0.0254402000
_diffrn_orient_matrix_UB_13      -0.0123352000
_diffrn_orient_matrix_UB_21      -0.0174272000
_diffrn_orient_matrix_UB_22      -0.0481909000
_diffrn_orient_matrix_UB_23      0.0136873000
_diffrn_orient_matrix_UB_31      -0.0191201000
_diffrn_orient_matrix_UB_32      -0.0083252000
_diffrn_orient_matrix_UB_33      -0.0416440000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3076
_reflns_number_total             4655
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4655
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0658
_refine_ls_restrained_S_all      1.041
_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)+(0.0817P)²+0.4202P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1757
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O001 O 0.57319(9) 0.60646(9) 0.39862(8) 0.0206(3) Uani 1 1 d . . . . .
O002 O 0.66968(9) 0.33274(10) 0.59592(8) 0.0234(3) Uani 1 1 d . . . . .
N003 N 0.55158(10) 0.15692(11) 0.14615(9) 0.0154(3) Uani 1 1 d . . . . .
N004 N 0.60923(9) 0.25834(11) 0.30010(9) 0.0156(3) Uani 1 1 d . . . . .
N005 N 0.79113(10) 0.35987(12) 0.29218(10) 0.0187(3) Uani 1 1 d . . . . .
C006 C 0.64684(11) 0.37205(13) 0.51661(11) 0.0171(4) Uani 1 1 d . . . . .
C007 C 0.74218(11) 0.31652(12) 0.22480(11) 0.0149(3) Uani 1 1 d . . . . .
C008 C 0.62418(11) 0.47639(13) 0.50263(11) 0.0167(4) Uani 1 1 d . . . . .
C009 C 0.59428(11) 0.43677(13) 0.35181(12) 0.0160(3) Uani 1 1 d . . . . .
C00A C 0.66152(11) 0.25528(12) 0.23539(11) 0.0138(3) Uani 1 1 d . . . . .
C00B C 0.63846(11) 0.18312(12) 0.16561(11) 0.0145(3) Uani 1 1 d . . . . .
C00C C 0.59750(11) 0.50676(12) 0.41974(11) 0.0166(4) Uani 1 1 d . . . . .
C00D C 0.69127(12) 0.12665(12) 0.11116(11) 0.0162(4) Uani 1 1 d . . . . .
C00E C 0.54870(12) 0.08774(13) 0.07977(11) 0.0169(4) Uani 1 1 d . . . . .
C00F C 0.64550(11) 0.30057(13) 0.44905(11) 0.0168(4) Uani 1 1 d . . . . .
C00G C 0.63462(12) 0.06632(13) 0.05726(12) 0.0180(4) Uani 1 1 d . . . . .
C00H C 0.61916(11) 0.33312(12) 0.36675(11) 0.0151(3) Uani 1 1 d . . . . .
C00I C 0.78497(12) 0.34227(13) 0.15032(12) 0.0191(4) Uani 1 1 d . . . . .
C00J C 0.86070(12) 0.40115(14) 0.17358(13) 0.0215(4) Uani 1 1 d . . . . .
C00K C 0.57052(13) 0.68155(14) 0.46660(13) 0.0223(4) Uani 1 1 d . . . . .
C00L C 0.86334(13) 0.40975(14) 0.26155(13) 0.0236(4) Uani 1 1 d . . . . .
C00M C 0.65395(15) 0.39755(16) 0.66906(13) 0.0250(4) Uani 1 1 d . . . . .
H00H H 0.6988(16) 0.4580(19) 0.6742(14) 0.035(6) Uiso 1 1 d . . . . .
H00E H 0.4907(15) 0.0627(17) 0.0547(13) 0.025(5) Uiso 1 1 d . . . . .
H00I H 0.7664(14) 0.3231(18) 0.0897(14) 0.028(6) Uiso 1 1 d . . . . .
H00D H 0.7565(15) 0.1288(16) 0.1121(13) 0.024(5) Uiso 1 1 d . . . . .
H005 H 0.7807(15) 0.3531(18) 0.3491(16) 0.034(6) Uiso 1 1 d . . . . .
H009 H 0.5732(13) 0.4573(15) 0.2928(13) 0.015(5) Uiso 1 1 d . . . . .
H00A H 0.5305(14) 0.6562(16) 0.5137(13) 0.025(5) Uiso 1 1 d . . . . .
H00F H 0.6603(14) 0.2245(17) 0.4610(13) 0.026(5) Uiso 1 1 d . . . . .
H008 H 0.6238(14) 0.5254(17) 0.5510(13) 0.024(5) Uiso 1 1 d . . . . .
H00G H 0.6537(14) 0.0205(17) 0.0116(13) 0.024(5) Uiso 1 1 d . . . . .
H003 H 0.5023(17) 0.182(2) 0.1721(16) 0.046(7) Uiso 1 1 d . . . . .
H00L H 0.9057(15) 0.4451(17) 0.3027(14) 0.030(6) Uiso 1 1 d . . . . .
H00B H 0.6325(14) 0.6960(16) 0.4886(13) 0.021(5) Uiso 1 1 d . . . . .
H00K H 0.6612(15) 0.3536(18) 0.7191(15) 0.033(6) Uiso 1 1 d . . . . .
H00M H 0.5910(15) 0.4221(16) 0.6686(14) 0.026(5) Uiso 1 1 d . . . . .
H00J H 0.9039(14) 0.4273(17) 0.1337(14) 0.028(6) Uiso 1 1 d . . . . .
H00C H 0.5440(15) 0.7444(18) 0.4365(14) 0.035(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00C 1.371(2) . ?
O001 C00K 1.435(2) . ?
O002 C006 1.369(2) . ?
O002 C00M 1.438(2) . ?
N003 C00B 1.379(2) . ?
N003 C00E 1.364(2) . ?
N003 H003 0.92(3) . ?
N004 C00A 1.302(2) . ?
N004 C00H 1.420(2) . ?
N005 C007 1.381(2) . ?
N005 C00L 1.366(2) . ?
N005 H005 0.91(2) . ?
C006 C008 1.401(2) . ?
C006 C00F 1.398(2) . ?
C007 C00A 1.465(2) . ?
C007 C00I 1.388(2) . ?
C008 C00C 1.396(3) . ?
C008 H008 0.98(2) . ?
C009 C00C 1.389(2) . ?
C009 C00H 1.403(2) . ?
C009 H009 1.00(2) . ?
C00A C00B 1.463(2) . ?
C00B C00D 1.389(2) . ?
C00D C00G 1.411(3) . ?
C00D H00D 0.99(2) . ?
C00E C00G 1.384(2) . ?
C00E H00E 1.00(2) . ?
C00F C00H 1.394(2) . ?
C00F H00F 1.02(2) . ?
C00G H00G 0.98(2) . ?
C00I C00J 1.409(3) . ?
C00I H00I 1.01(2) . ?
C00J C00L 1.374(3) . ?
C00J H00J 0.98(2) . ?
C00K H00A 1.02(2) . ?
C00K H00B 1.00(2) . ?
C00K H00C 1.01(2) . ?
C00L H00L 1.00(2) . ?
C00M H00H 1.03(2) . ?
C00M H00K 0.97(2) . ?
C00M H00M 1.00(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00C O001 C00K 117.81(14) . . ?
C006 O002 C00M 117.24(14) . . ?
C00B N003 H003 126.6(16) . . ?
C00E N003 C00B 109.39(14) . . ?
C00E N003 H003 124.0(16) . . ?
C00A N004 C00H 122.35(14) . . ?
C007 N005 H005 126.6(15) . . ?
C00L N005 C007 109.72(16) . . ?
C00L N005 H005 123.6(15) . . ?
O002 C006 C008 123.19(16) . . ?
O002 C006 C00F 115.70(15) . . ?
C00F C006 C008 121.10(16) . . ?
N005 C007 C00A 123.87(15) . . ?
N005 C007 C00I 106.67(15) . . ?
C00I C007 C00A 129.46(16) . . ?
C006 C008 H008 120.3(12) . . ?
C00C C008 C006 118.27(16) . . ?
C00C C008 H008 121.3(12) . . ?
C00C C009 C00H 119.18(16) . . ?
C00C C009 H009 122.1(11) . . ?
C00H C009 H009 118.7(11) . . ?
N004 C00A C007 126.84(15) . . ?
N004 C00A C00B 117.34(14) . . ?
C00B C00A C007 115.82(14) . . ?
N003 C00B C00A 121.30(14) . . ?
N003 C00B C00D 107.44(15) . . ?
C00D C00B C00A 131.20(16) . . ?
O001 C00C C008 123.41(15) . . ?
O001 C00C C009 114.92(16) . . ?
C009 C00C C008 121.68(15) . . ?
C00B C00D C00G 107.58(15) . . ?
C00B C00D H00D 124.8(12) . . ?
C00G C00D H00D 127.6(12) . . ?
N003 C00E C00G 108.43(16) . . ?
N003 C00E H00E 120.8(12) . . ?
C00G C00E H00E 130.8(12) . . ?
C006 C00F H00F 119.8(12) . . ?
C00H C00F C006 119.44(15) . . ?
C00H C00F H00F 120.7(12) . . ?
C00D C00G H00G 125.3(13) . . ?
C00E C00G C00D 107.14(15) . . ?
C00E C00G H00G 127.5(13) . . ?
C009 C00H N004 120.12(16) . . ?
C00F C00H N004 119.27(14) . . ?
C00F C00H C009 120.31(15) . . ?
C007 C00I C00J 108.08(16) . . ?
C007 C00I H00I 127.1(13) . . ?
C00J C00I H00I 124.8(13) . . ?
C00I C00J H00J 125.2(13) . . ?
C00L C00J C00I 107.19(16) . . ?
C00L C00J H00J 127.6(13) . . ?
O001 C00K H00A 110.4(12) . . ?
O001 C00K H00B 109.1(12) . . ?
O001 C00K H00C 102.6(13) . . ?
H00A C00K H00B 112.4(16) . . ?
H00A C00K H00C 110.8(18) . . ?
H00B C00K H00C 111.1(18) . . ?
N005 C00L C00J 108.33(17) . . ?
N005 C00L H00L 119.4(12) . . ?
C00J C00L H00L 132.2(12) . . ?
O002 C00M H00H 111.8(13) . . ?
O002 C00M H00K 106.4(13) . . ?
O002 C00M H00M 111.1(12) . . ?
H00H C00M H00K 108.8(19) . . ?
H00H C00M H00M 112.5(18) . . ?
H00K C00M H00M 105.8(19) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_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
-19 9 0 0.0662 -18.7512 8.5843 0.0899 -0.9552 -0.0857 0.2833
-14 13 1 0.0640 -14.3914 13.3726 0.5088 -0.9111 -0.3867 0.1426
15 -13 1 0.0731 14.8424 -12.9248 1.2755 0.8954 0.3817 -0.2293
10 -16 4 0.0829 9.8045 -15.6977 4.0152 0.7345 0.6406 -0.2240
0 -18 -3 0.0815 0.2320 -17.9766 -2.9347 0.5026 0.8221 0.2674
-4 -18 3 0.0712 -4.4860 -17.5305 3.3921 0.2281 0.9694 0.0905
5 18 -2 0.0681 5.1114 17.5711 -1.5738 -0.2271 -0.9574 -0.1785
-11 -15 4 0.0760 -10.8736 -15.3709 3.5687 -0.0796 0.9791 0.1873
16 12 -5 0.0738 15.5576 11.7002 -5.4558 0.3800 -0.9096 -0.1677
-20 -7 2 0.0753 -19.5087 -7.1616 2.1399 -0.6096 0.7144 0.3435
17 -10 -7 0.0848 16.5614 -9.8868 -7.4647 0.9934 0.0857 0.0765
-18 9 2 0.0681 -18.4329 8.9836 2.2779 -0.9799 -0.0805 0.1828
-14 14 3 0.0672 -13.5339 13.8364 3.1165 -0.9214 -0.3883 0.0138
-8 17 2 0.0655 -7.6569 16.8723 1.9369 -0.7535 -0.6531 -0.0747
9 -17 0 0.0653 8.6385 -16.5732 0.3698 0.7560 0.6532 -0.0426
-4 -15 -12 0.1276 -3.9068 -14.9524 -11.6151 0.3704 0.6297 0.6829
-1 18 1 0.0644 -0.9498 18.1106 0.8186 -0.5081 -0.8450 -0.1667
-5 -18 2 0.0681 -5.0634 -17.5515 2.0446 0.2226 0.9620 0.1578
-6 3 -20 0.2010 -6.4262 3.4293 -20.2932 -0.0890 -0.3310 0.9394
12 15 -1 0.0704 11.5749 15.2010 -1.3881 0.0845 -0.9533 -0.2901
-17 -11 0 0.0661 -16.5642 -11.3638 -0.3839 -0.3561 0.8310 0.4273
-16 -10 -7 0.1086 -16.1407 -10.0487 -6.9700 -0.2917 0.6701 0.6825
16 12 -3 0.0699 16.1134 11.6312 -3.3378 0.3775 -0.8870 -0.2659
8 3 20 0.1804 8.2921 2.6628 19.6707 0.0150 -0.0036 -0.9999
19 7 -4 0.0736 19.3713 6.9399 -4.2062 0.6354 -0.7296 -0.2530
4 1 21 0.1936 3.7682 0.9489 21.4479 -0.1409 0.1822 -0.9731
21 2 -4 0.0778 21.0162 1.6536 -3.6341 0.8273 -0.4957 -0.2643

_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_mf006
_database_code_depnum_ccdc_archive 'CCDC 1896808'
loop_
_audit_author_name
_audit_author_address
'Milosz Pawlicki'
;Department of Chemistry University of Wroclaw
Poland
;
_audit_update_record             
;
2019-02-12 deposited with the CCDC.	2019-04-25 downloaded from the CCDC.
;
_audit_creation_date             2019-01-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 B F2 N3 O2, C2 H3 N'
_chemical_formula_sum            'C19 H17 B F2 N4 O2'
_chemical_formula_weight         382.17
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.1859(4)
_cell_length_b                   12.0427(7)
_cell_length_c                   12.0895(9)
_cell_angle_alpha                93.791(5)
_cell_angle_beta                 100.927(5)
_cell_angle_gamma                98.538(5)
_cell_volume                     1011.05(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1917
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.5860
_cell_measurement_theta_min      2.2710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.568
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.136
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.862
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6891
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.762
_diffrn_reflns_theta_min         1.718
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.862
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  94.00   1.00    7.50    --   15.81  77.00 -90.00   93
  2  ω     -7.00  97.00   1.00    7.50    --   15.81  77.00 150.00  104
  3  ω    -56.00  44.00   1.00    7.50    --  -16.75  77.00  30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0050883000
_diffrn_orient_matrix_UB_12      -0.0579359000
_diffrn_orient_matrix_UB_13      0.0045796000
_diffrn_orient_matrix_UB_21      -0.1012144000
_diffrn_orient_matrix_UB_22      -0.0135059000
_diffrn_orient_matrix_UB_23      -0.0180686000
_diffrn_orient_matrix_UB_31      0.0107902000
_diffrn_orient_matrix_UB_32      -0.0064846000
_diffrn_orient_matrix_UB_33      -0.0570708000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3331
_reflns_number_total             4547
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.018
_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)+(0.0600P)²+0.1304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1299
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H005(0.018) H00G(0.02) H00I(0.022) H00K(0.023) H00L(0.023)
 H00M(0.024) H00N(0.025) H00P(0.029) H00A(0.033) H00B(0.033) H00C(0.033)
 H00D(0.04) H00E(0.04) H00F(0.04) H00H(0.078) H00J(0.078) H00O(0.078)
 Fixed X: H005(0.297272) H00G(0.219505) H00I(0.282855) H00K(0.12532)
 H00L(0.346411) H00M(0.367631) H00N(0.458106) H00P(0.44936) H00A(0.060139)
 H00B(0.27346) H00C(0.108082) H00D(0.130806) H00E(0.007771) H00F(0.221522)
 H00H(0.092691) H00J(0.305871) H00O(0.252564)
 Fixed Y: H005(0.67549) H00G(0.571343) H00I(0.280342) H00K(0.231761)
 H00L(0.405719) H00M(0.873306) H00N(0.888587) H00P(1.005015) H00A(0.533312)
 H00B(0.519202) H00C(0.45959) H00D(0.050216) H00E(0.105119) H00F(0.09499)
 H00H(0.835505) H00J(0.895602) H00O(0.764978)
 Fixed Z: H005(0.524767) H00G(0.671214) H00I(0.227543) H00K(0.616665)
 H00L(0.08106) H00M(0.4603) H00N(0.144014) H00P(0.317573) H00A(0.810552)
 H00B(0.856998) H00C(0.911042) H00D(0.385991) H00E(0.461728) H00F(0.512324)
 H00H(0.859722) H00J(0.902204) H00O(0.905425)
;
_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
F001 F 0.19873(14) 0.65114(8) 0.05183(8) 0.0239(3) Uani 1 1 d . . . . .
F002 F 0.52045(15) 0.65924(8) 0.07805(9) 0.0250(3) Uani 1 1 d . . . . .
O003 O 0.11909(17) 0.38499(10) 0.76290(10) 0.0210(3) Uani 1 1 d . . . . .
O004 O 0.19661(18) 0.21598(10) 0.41100(10) 0.0228(3) Uani 1 1 d . . . . .
N005 N 0.29172(19) 0.61750(11) 0.47803(11) 0.0153(3) Uani 1 1 d . . . . .
H005 H 0.297272 0.675490 0.524767 0.018 Uiso 1 1 calc R . . . .
N006 N 0.3472(2) 0.54042(11) 0.19277(12) 0.0163(3) Uani 1 1 d . . . . .
N007 N 0.3926(2) 0.74942(12) 0.22577(12) 0.0173(3) Uani 1 1 d . . . . .
N008 N 0.2876(2) 0.79451(13) 0.66102(14) 0.0281(4) Uani 1 1 d . . . . .
C00A C 0.2515(2) 0.51136(14) 0.51465(14) 0.0148(3) Uani 1 1 d . . . . .
C00B C 0.3225(2) 0.63502(14) 0.37374(14) 0.0154(3) Uani 1 1 d . . . . .
C00C C 0.2458(2) 0.41362(14) 0.44202(14) 0.0158(3) Uani 1 1 d . . . . .
C00D C 0.2837(2) 0.42776(14) 0.33108(14) 0.0165(4) Uani 1 1 d . . . . .
C00E C 0.3178(2) 0.53915(14) 0.30193(14) 0.0157(3) Uani 1 1 d . . . . .
C00F C 0.1650(2) 0.40161(14) 0.66010(14) 0.0172(4) Uani 1 1 d . . . . .
C00G C 0.2128(2) 0.50589(14) 0.62427(14) 0.0163(3) Uani 1 1 d . . . . .
H00G H 0.219505 0.571343 0.671214 0.020 Uiso 1 1 calc R . . . .
C00H C 0.1977(2) 0.30754(14) 0.48430(15) 0.0175(4) Uani 1 1 d . . . . .
C00I C 0.2964(2) 0.35864(15) 0.23488(14) 0.0186(4) Uani 1 1 d . . . . .
H00I H 0.282855 0.280342 0.227543 0.022 Uiso 1 1 calc R . . . .
C00J C 0.3615(2) 0.74410(14) 0.33544(14) 0.0160(3) Uani 1 1 d . . . . .
C00K C 0.1575(2) 0.30159(14) 0.59059(15) 0.0188(4) Uani 1 1 d . . . . .
H00K H 0.125320 0.231761 0.616665 0.023 Uiso 1 1 calc R . . . .
C00L C 0.3331(2) 0.42999(14) 0.15337(15) 0.0188(4) Uani 1 1 d . . . . .
H00L H 0.346411 0.405719 0.081060 0.023 Uiso 1 1 calc R . . . .
C00M C 0.3815(2) 0.85309(14) 0.38709(15) 0.0200(4) Uani 1 1 d . . . . .
H00M H 0.367631 0.873306 0.460300 0.024 Uiso 1 1 calc R . . . .
C00N C 0.4318(2) 0.86085(14) 0.21036(15) 0.0206(4) Uani 1 1 d . . . . .
H00N H 0.458106 0.888587 0.144014 0.025 Uiso 1 1 calc R . . . .
C00O C 0.2610(3) 0.80954(15) 0.75031(17) 0.0251(4) Uani 1 1 d . . . . .
C00P C 0.4269(3) 0.92660(15) 0.30716(16) 0.0238(4) Uani 1 1 d . . . . .
H00P H 0.449360 1.005015 0.317573 0.029 Uiso 1 1 calc R . . . .
C00Q C 0.1421(3) 0.48227(15) 0.84186(15) 0.0218(4) Uani 1 1 d . . . . .
H00A H 0.060139 0.533312 0.810552 0.033 Uiso 1 1 calc GR . . . .
H00B H 0.273460 0.519202 0.856998 0.033 Uiso 1 1 calc GR . . . .
H00C H 0.108082 0.459590 0.911042 0.033 Uiso 1 1 calc GR . . . .
C00R C 0.1340(3) 0.10766(15) 0.44561(17) 0.0268(4) Uani 1 1 d . . . . .
H00D H 0.130806 0.050216 0.385991 0.040 Uiso 1 1 calc GR . . . .
H00E H 0.007771 0.105119 0.461728 0.040 Uiso 1 1 calc GR . . . .
H00F H 0.221522 0.094990 0.512324 0.040 Uiso 1 1 calc GR . . . .
B00S B 0.3662(3) 0.64995(17) 0.13279(17) 0.0187(4) Uani 1 1 d . . . . .
C00U C 0.2250(4) 0.8280(2) 0.86411(18) 0.0521(7) Uani 1 1 d . . . . .
H00H H 0.092691 0.835505 0.859722 0.078 Uiso 1 1 calc GR . . . .
H00J H 0.305871 0.895602 0.902204 0.078 Uiso 1 1 calc GR . . . .
H00O H 0.252564 0.764978 0.905425 0.078 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
F001 B00S 1.402(2) . ?
F002 B00S 1.390(2) . ?
O003 C00F 1.3645(19) . ?
O003 C00Q 1.430(2) . ?
O004 C00H 1.366(2) . ?
O004 C00R 1.431(2) . ?
N005 H005 0.8600 . ?
N005 C00A 1.388(2) . ?
N005 C00B 1.345(2) . ?
N006 C00E 1.376(2) . ?
N006 C00L 1.365(2) . ?
N006 B00S 1.547(2) . ?
N007 C00J 1.390(2) . ?
N007 C00N 1.362(2) . ?
N007 B00S 1.552(2) . ?
N008 C00O 1.139(2) . ?
C00A C00C 1.412(2) . ?
C00A C00G 1.409(2) . ?
C00B C00E 1.390(2) . ?
C00B C00J 1.428(2) . ?
C00C C00D 1.434(2) . ?
C00C C00H 1.426(2) . ?
C00D C00E 1.408(2) . ?
C00D C00I 1.410(2) . ?
C00F C00G 1.372(2) . ?
C00F C00K 1.411(2) . ?
C00G H00G 0.9300 . ?
C00H C00K 1.374(2) . ?
C00I H00I 0.9300 . ?
C00I C00L 1.386(2) . ?
C00J C00M 1.391(2) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00P 1.404(2) . ?
C00N H00N 0.9300 . ?
C00N C00P 1.378(2) . ?
C00O C00U 1.456(3) . ?
C00P H00P 0.9300 . ?
C00Q H00A 0.9600 . ?
C00Q H00B 0.9600 . ?
C00Q H00C 0.9600 . ?
C00R H00D 0.9600 . ?
C00R H00E 0.9600 . ?
C00R H00F 0.9600 . ?
C00U H00H 0.9600 . ?
C00U H00J 0.9600 . ?
C00U H00O 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
C00F O003 C00Q 117.36(13) . . ?
C00H O004 C00R 116.59(13) . . ?
C00A N005 H005 118.1 . . ?
C00B N005 H005 118.1 . . ?
C00B N005 C00A 123.88(14) . . ?
C00E N006 B00S 122.46(14) . . ?
C00L N006 C00E 105.66(14) . . ?
C00L N006 B00S 131.49(14) . . ?
C00J N007 B00S 127.49(14) . . ?
C00N N007 C00J 106.76(14) . . ?
C00N N007 B00S 125.43(14) . . ?
N005 C00A C00C 120.17(14) . . ?
N005 C00A C00G 117.59(15) . . ?
C00G C00A C00C 122.22(15) . . ?
N005 C00B C00E 116.23(15) . . ?
N005 C00B C00J 123.97(15) . . ?
C00E C00B C00J 119.79(15) . . ?
C00A C00C C00D 118.14(15) . . ?
C00A C00C C00H 116.96(15) . . ?
C00H C00C C00D 124.88(15) . . ?
C00E C00D C00C 116.82(15) . . ?
C00E C00D C00I 105.44(14) . . ?
C00I C00D C00C 137.74(16) . . ?
N006 C00E C00B 124.50(15) . . ?
N006 C00E C00D 110.79(14) . . ?
C00B C00E C00D 124.71(15) . . ?
O003 C00F C00G 124.04(15) . . ?
O003 C00F C00K 114.50(14) . . ?
C00G C00F C00K 121.46(15) . . ?
C00A C00G H00G 120.8 . . ?
C00F C00G C00A 118.37(15) . . ?
C00F C00G H00G 120.8 . . ?
O004 C00H C00C 114.41(14) . . ?
O004 C00H C00K 124.46(15) . . ?
C00K C00H C00C 121.12(15) . . ?
C00D C00I H00I 126.6 . . ?
C00L C00I C00D 106.73(15) . . ?
C00L C00I H00I 126.6 . . ?
N007 C00J C00B 117.67(14) . . ?
N007 C00J C00M 109.16(14) . . ?
C00M C00J C00B 133.14(16) . . ?
C00F C00K H00K 120.1 . . ?
C00H C00K C00F 119.86(15) . . ?
C00H C00K H00K 120.1 . . ?
N006 C00L C00I 111.37(15) . . ?
N006 C00L H00L 124.3 . . ?
C00I C00L H00L 124.3 . . ?
C00J C00M H00M 126.7 . . ?
C00J C00M C00P 106.61(16) . . ?
C00P C00M H00M 126.7 . . ?
N007 C00N H00N 124.9 . . ?
N007 C00N C00P 110.28(15) . . ?
C00P C00N H00N 124.9 . . ?
N008 C00O C00U 179.4(2) . . ?
C00M C00P H00P 126.4 . . ?
C00N C00P C00M 107.19(16) . . ?
C00N C00P H00P 126.4 . . ?
O003 C00Q H00A 109.5 . . ?
O003 C00Q H00B 109.5 . . ?
O003 C00Q H00C 109.5 . . ?
H00A C00Q H00B 109.5 . . ?
H00A C00Q H00C 109.5 . . ?
H00B C00Q H00C 109.5 . . ?
O004 C00R H00D 109.5 . . ?
O004 C00R H00E 109.5 . . ?
O004 C00R H00F 109.5 . . ?
H00D C00R H00E 109.5 . . ?
H00D C00R H00F 109.5 . . ?
H00E C00R H00F 109.5 . . ?
F001 B00S N006 110.12(15) . . ?
F001 B00S N007 109.59(14) . . ?
F002 B00S F001 108.07(15) . . ?
F002 B00S N006 111.59(14) . . ?
F002 B00S N007 110.87(15) . . ?
N006 B00S N007 106.60(14) . . ?
C00O C00U H00H 109.5 . . ?
C00O C00U H00J 109.5 . . ?
C00O C00U H00O 109.5 . . ?
H00H C00U H00J 109.5 . . ?
H00H C00U H00O 109.5 . . ?
H00J C00U H00O 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 182.8 52.1 ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.053
_oxdiff_exptl_absorpt_empirical_full_min 0.966
####################################################################### 
# 
# 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_mjp_test
_database_code_depnum_ccdc_archive 'CCDC 1896809'
loop_
_audit_author_name
_audit_author_address
'Milosz Pawlicki'
;Department of Chemistry University of Wroclaw
Poland
;
_audit_update_record             
;
2019-02-12 deposited with the CCDC.	2019-04-25 downloaded from the CCDC.
;
_audit_creation_date             2018-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 N3 O2, 0.5(H2 O)'
_chemical_formula_sum            'C17 H16 N3 O2.50'
_chemical_formula_weight         302.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H16 N2 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.6680(14)
_cell_length_b                   24.498(4)
_cell_length_c                   11.286(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.034(12)
_cell_angle_gamma                90
_cell_volume                     2945.4(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    609
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.1960
_cell_measurement_theta_min      1.9060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.0827
_exptl_crystal_size_mid          0.0632
_exptl_crystal_size_min          0.0486
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1393
_diffrn_reflns_av_unetI/netI     0.3222
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10639
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.912
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3456
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -21.00   90.00   1.0000  350.0000
omega____ theta____ kappa____ phi______ frames
    -       15.5804   57.0000   90.0000 111

#__ type_ start__ end____ width___ exp.time_
  2 omega  -92.00  -36.00   1.0000  350.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.4398 -178.0000 -150.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega -110.00  -87.00   1.0000  350.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.4398 -178.0000   90.0000 23
;
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0139620000
_diffrn_orient_matrix_UB_12      -0.0282062000
_diffrn_orient_matrix_UB_13      -0.0047790000
_diffrn_orient_matrix_UB_21      0.0116260000
_diffrn_orient_matrix_UB_22      -0.0014519000
_diffrn_orient_matrix_UB_23      0.0623536000
_diffrn_orient_matrix_UB_31      -0.0640674000
_diffrn_orient_matrix_UB_32      -0.0064276000
_diffrn_orient_matrix_UB_33      0.0067552000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1841
_reflns_number_total             5183
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.49
_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, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.799
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2527
_refine_ls_R_factor_gt           0.0753
_refine_ls_restrained_S_all      0.799
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1374
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H006(0.02) H008(0.023) H009(0.025) H00I(0.022) H00N(0.018)
 H00S(0.017) H00V(0.021) H00A(0.027) H00C(0.027) H00D(0.027) H00X(0.02)
 H00Y(0.024) H00Z(0.027) H010(0.022) H012(0.025) H013(0.027) H014(0.021)
 H015(0.026) H016(0.029) H01A(0.044) H01B(0.044) H01C(0.044) H01D(0.045)
 H01E(0.045) H01F(0.045) H01G(0.049) H01H(0.049) H01I(0.049)
 Fixed X: H006(0.516071) H008(0.569826) H009(0.610765) H00I(0.119695)
 H00N(0.332659) H00S(0.279927) H00V(0.728757) H00A(0.192705) H00C(0.066219)
 H00D(0.136162) H00X(0.653531) H00Y(0.477531) H00Z(0.829238) H010(0.122587)
 H012(0.826533) H013(0.686622) H014(-0.051947) H015(0.863866) H016(0.292836)
 H01A(-0.143165) H01B(-0.165074) H01C(-0.091716) H01D(0.173141) H01E(0.156588)
 H01F(0.287548) H01G(0.027309) H01H(0.081735) H01I(0.122673)
 Fixed Y: H006(0.414926) H008(0.603378) H009(0.176541) H00I(0.507328)
 H00N(0.65618) H00S(0.078546) H00V(0.54486) H00A(-0.003349) H00C(-0.017579)
 H00D(0.037038) H00X(0.255404) H00Y(0.684725) H00Z(0.199817) H010(0.262192)
 H012(0.482171) H013(0.402043) H014(0.094927) H015(0.248986) H016(0.32921)
 H01A(0.179464) H01B(0.154434) H01C(0.121112) H01D(0.340614) H01E(0.329826)
 H01F(0.34773) H01G(0.587513) H01H(0.64592) H01I(0.596655)
 Fixed Z: H006(0.115788) H008(0.168494) H009(0.698193) H00I(0.621712)
 H00N(0.397739) H00S(0.655047) H00V(0.161848) H00A(0.694347) H00C(0.751937)
 H00D(0.785114) H00X(0.400388) H00Y(0.245334) H00Z(0.700343) H010(0.28503)
 H012(0.01726) H013(-0.013468) H014(0.468794) H015(0.514491) H016(0.2672)
 H01A(0.231761) H01B(0.356817) H01C(0.264218) H01D(0.523254) H01E(0.658445)
 H01F(0.614964) H01G(0.569585) H01H(0.596434) H01I(0.678266)
;
_atom_sites_solution_hydrogens   mixed
_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
O001 O 0.0476(3) 0.03878(15) 0.6264(3) 0.0168(10) Uani 1 1 d . . . . .
O002 O 0.0089(3) 0.18073(15) 0.3406(3) 0.0195(10) Uani 1 1 d . . . . .
O003 O 0.2022(3) 0.59647(15) 0.5244(3) 0.0196(10) Uani 1 1 d . . . . .
O004 O 0.5739(5) 0.36448(18) 0.3468(4) 0.0193(11) Uani 1 1 d . . . . .
O005 O 0.1651(3) 0.40836(16) 0.6182(3) 0.0234(10) Uani 1 1 d . . . . .
N006 N 0.5765(4) 0.43779(19) 0.1096(4) 0.0170(12) Uani 1 1 d . . . . .
H006 H 0.516071 0.414926 0.115788 0.020 Uiso 1 1 calc R . . . .
N007 N 0.4019(4) 0.15628(18) 0.5652(4) 0.0128(11) Uani 1 1 d . . . . .
N008 N 0.5164(4) 0.60347(19) 0.2229(4) 0.0193(12) Uani 1 1 d . . . . .
H008 H 0.569826 0.603378 0.168494 0.023 Uiso 1 1 calc R . . . .
N009 N 0.6447(4) 0.19420(19) 0.6424(4) 0.0206(12) Uani 1 1 d . . . . .
H009 H 0.610765 0.176541 0.698193 0.025 Uiso 1 1 calc R . . . .
N00A N 0.4489(4) 0.46338(19) 0.3231(4) 0.0151(12) Uani 1 1 d . . . . .
N00B N 0.4010(5) 0.2813(2) 0.3813(5) 0.0200(13) Uani 1 1 d . . . . .
C00C C 0.2501(5) 0.2185(2) 0.4007(5) 0.0119(13) Uani 1 1 d . . . . .
C00D C 0.3870(5) 0.5745(2) 0.3614(5) 0.0135(14) Uani 1 1 d . . . . .
C00E C 0.3635(5) 0.4779(2) 0.4067(5) 0.0156(14) Uani 1 1 d . . . . .
C00F C 0.4717(5) 0.5577(2) 0.2782(5) 0.0148(14) Uani 1 1 d . . . . .
C00G C 0.4481(5) 0.2001(2) 0.5142(5) 0.0148(14) Uani 1 1 d . . . . .
C00H C 0.1988(5) 0.1714(2) 0.4524(5) 0.0122(13) Uani 1 1 d . . . . .
C00I C 0.1824(5) 0.5004(2) 0.5696(5) 0.0181(15) Uani 1 1 d . . . . .
H00I H 0.119695 0.507328 0.621712 0.022 Uiso 1 1 calc R . . . .
C00J C 0.3753(5) 0.2331(2) 0.4370(5) 0.0148(14) Uani 1 1 d . . . . .
C00K C 0.3287(4) 0.5329(2) 0.4271(5) 0.0130(14) Uani 1 1 d . . . . .
C00L C 0.2752(5) 0.1428(2) 0.5368(5) 0.0156(14) Uani 1 1 d . . . . .
C00M C 0.3119(5) 0.4347(2) 0.4721(5) 0.0134(14) Uani 1 1 d . . . . .
C00N C 0.3815(5) 0.6332(2) 0.3536(5) 0.0148(14) Uani 1 1 d . . . . .
H00N H 0.332659 0.656180 0.397739 0.018 Uiso 1 1 calc R . . . .
C00O C 0.5826(5) 0.2130(2) 0.5409(5) 0.0169(14) Uani 1 1 d . . . . .
C00P C 0.5010(5) 0.5024(2) 0.2600(5) 0.0172(15) Uani 1 1 d . . . . .
C00Q C 0.1065(5) 0.0819(2) 0.5737(5) 0.0170(14) Uani 1 1 d . . . . .
C00R C 0.5887(5) 0.4860(2) 0.1706(5) 0.0158(14) Uani 1 1 d . . . . .
C00S C 0.2292(5) 0.0973(2) 0.5992(5) 0.0144(14) Uani 1 1 d . . . . .
H00S H 0.279927 0.078546 0.655047 0.017 Uiso 1 1 calc R . . . .
C00T C 0.0748(5) 0.1512(2) 0.4261(5) 0.0166(15) Uani 1 1 d . . . . .
C00U C 0.2231(5) 0.4466(2) 0.5514(5) 0.0203(15) Uani 1 1 d . . . . .
C00V C 0.6976(4) 0.5112(2) 0.1359(5) 0.0178(14) Uani 1 1 d . . . . .
H00V H 0.728757 0.544860 0.161848 0.021 Uiso 1 1 calc R . . . .
C00W C 0.1164(4) 0.0114(2) 0.7225(5) 0.0183(14) Uani 1 1 d . . . . .
H00A H 0.192705 -0.003349 0.694347 0.027 Uiso 1 1 calc GR . . . .
H00C H 0.066219 -0.017579 0.751937 0.027 Uiso 1 1 calc GR . . . .
H00D H 0.136162 0.037038 0.785114 0.027 Uiso 1 1 calc GR . . . .
C00X C 0.6694(5) 0.2388(2) 0.4738(5) 0.0170(14) Uani 1 1 d . . . . .
H00X H 0.653531 0.255404 0.400388 0.020 Uiso 1 1 calc R . . . .
C00Y C 0.4624(5) 0.6490(2) 0.2682(5) 0.0203(15) Uani 1 1 d . . . . .
H00Y H 0.477531 0.684725 0.245334 0.024 Uiso 1 1 calc R . . . .
C00Z C 0.7682(5) 0.2078(2) 0.6410(5) 0.0227(16) Uani 1 1 d . . . . .
H00Z H 0.829238 0.199817 0.700343 0.027 Uiso 1 1 calc R . . . .
C010 C 0.2024(5) 0.2605(2) 0.3223(5) 0.0181(15) Uani 1 1 d . . . . .
H010 H 0.122587 0.262192 0.285030 0.022 Uiso 1 1 calc R . . . .
C011 C 0.2350(5) 0.5420(2) 0.5108(5) 0.0174(15) Uani 1 1 d . . . . .
C012 C 0.7517(5) 0.4761(2) 0.0539(5) 0.0212(15) Uani 1 1 d . . . . .
H012 H 0.826533 0.482171 0.017260 0.025 Uiso 1 1 calc R . . . .
C013 C 0.6744(5) 0.4312(3) 0.0373(5) 0.0224(16) Uani 1 1 d . . . . .
H013 H 0.686622 0.402043 -0.013468 0.027 Uiso 1 1 calc R . . . .
C014 C 0.0292(5) 0.1075(2) 0.4861(5) 0.0172(14) Uani 1 1 d . . . . .
H014 H -0.051947 0.094927 0.468794 0.021 Uiso 1 1 calc R . . . .
C015 C 0.7878(5) 0.2353(2) 0.5381(5) 0.0220(16) Uani 1 1 d . . . . .
H015 H 0.863866 0.248986 0.514491 0.026 Uiso 1 1 calc R . . . .
C016 C 0.2977(5) 0.2976(2) 0.3130(5) 0.0242(16) Uani 1 1 d . . . . .
H016 H 0.292836 0.329210 0.267200 0.029 Uiso 1 1 calc R . . . .
C017 C -0.1075(5) 0.1569(2) 0.2945(5) 0.0293(17) Uani 1 1 d . . . . .
H01A H -0.143165 0.179464 0.231761 0.044 Uiso 1 1 calc GR . . . .
H01B H -0.165074 0.154434 0.356817 0.044 Uiso 1 1 calc GR . . . .
H01C H -0.091716 0.121112 0.264218 0.044 Uiso 1 1 calc GR . . . .
C018 C 0.1984(5) 0.3519(2) 0.6024(6) 0.0302(17) Uani 1 1 d . . . . .
H01D H 0.173141 0.340614 0.523254 0.045 Uiso 1 1 calc GR . . . .
H01E H 0.156588 0.329826 0.658445 0.045 Uiso 1 1 calc GR . . . .
H01F H 0.287548 0.347730 0.614964 0.045 Uiso 1 1 calc GR . . . .
C019 C 0.1001(5) 0.6076(2) 0.5983(5) 0.0327(18) Uani 1 1 d . . . . .
H01G H 0.027309 0.587513 0.569585 0.049 Uiso 1 1 calc GR . . . .
H01H H 0.081735 0.645920 0.596434 0.049 Uiso 1 1 calc GR . . . .
H01I H 0.122673 0.596655 0.678266 0.049 Uiso 1 1 calc GR . . . .
H00B H 0.461(4) 0.302(2) 0.391(4) 0.008(16) Uiso 1 1 d . . . . .
H00E H 0.540(5) 0.393(2) 0.333(5) 0.02(2) Uiso 1 1 d . . . . .
H00F H 0.634(5) 0.371(3) 0.387(5) 0.04(2) Uiso 1 1 d . . . . .
H00M H 0.343(4) 0.3999(19) 0.455(4) 0.008(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00Q 1.380(6) . ?
O001 C00W 1.442(5) . ?
O002 C00T 1.370(6) . ?
O002 C017 1.444(5) . ?
O003 C011 1.389(6) . ?
O003 C019 1.433(6) . ?
O004 H00E 0.79(5) . ?
O004 H00F 0.79(5) . ?
O005 C00U 1.371(6) . ?
O005 C018 1.441(6) . ?
N006 H006 0.8600 . ?
N006 C00R 1.370(7) . ?
N006 C013 1.368(6) . ?
N007 C00G 1.326(6) . ?
N007 C00L 1.412(6) . ?
N008 H008 0.8600 . ?
N008 C00F 1.381(6) . ?
N008 C00Y 1.366(6) . ?
N009 H009 0.8600 . ?
N009 C00O 1.372(6) . ?
N009 C00Z 1.360(6) . ?
N00A C00E 1.392(6) . ?
N00A C00P 1.331(7) . ?
N00B C00J 1.371(7) . ?
N00B C016 1.371(6) . ?
N00B H00B 0.81(4) . ?
C00C C00H 1.415(7) . ?
C00C C00J 1.422(6) . ?
C00C C010 1.433(7) . ?
C00D C00F 1.399(7) . ?
C00D C00K 1.423(7) . ?
C00D C00N 1.441(7) . ?
C00E C00K 1.421(7) . ?
C00E C00M 1.418(8) . ?
C00F C00P 1.407(7) . ?
C00G C00J 1.395(7) . ?
C00G C00O 1.485(7) . ?
C00H C00L 1.408(7) . ?
C00H C00T 1.428(7) . ?
C00I H00I 0.9300 . ?
C00I C00U 1.406(7) . ?
C00I C011 1.355(7) . ?
C00K C011 1.429(7) . ?
C00L C00S 1.420(7) . ?
C00M C00U 1.369(7) . ?
C00M H00M 0.94(4) . ?
C00N H00N 0.9300 . ?
C00N C00Y 1.381(7) . ?
C00O C00X 1.380(7) . ?
C00P C00R 1.467(7) . ?
C00Q C00S 1.377(6) . ?
C00Q C014 1.402(7) . ?
C00R C00V 1.390(7) . ?
C00S H00S 0.9300 . ?
C00T C014 1.370(7) . ?
C00V H00V 0.9300 . ?
C00V C012 1.409(7) . ?
C00W H00A 0.9600 . ?
C00W H00C 0.9600 . ?
C00W H00D 0.9600 . ?
C00X H00X 0.9300 . ?
C00X C015 1.426(7) . ?
C00Y H00Y 0.9300 . ?
C00Z H00Z 0.9300 . ?
C00Z C015 1.368(7) . ?
C010 H010 0.9300 . ?
C010 C016 1.373(7) . ?
C012 H012 0.9300 . ?
C012 C013 1.382(7) . ?
C013 H013 0.9300 . ?
C014 H014 0.9300 . ?
C015 H015 0.9300 . ?
C016 H016 0.9300 . ?
C017 H01A 0.9600 . ?
C017 H01B 0.9600 . ?
C017 H01C 0.9600 . ?
C018 H01D 0.9600 . ?
C018 H01E 0.9600 . ?
C018 H01F 0.9600 . ?
C019 H01G 0.9600 . ?
C019 H01H 0.9600 . ?
C019 H01I 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
C00Q O001 C00W 117.0(4) . . ?
C00T O002 C017 116.1(4) . . ?
C011 O003 C019 116.7(4) . . ?
H00E O004 H00F 107(6) . . ?
C00U O005 C018 117.8(4) . . ?
C00R N006 H006 124.9 . . ?
C013 N006 H006 124.9 . . ?
C013 N006 C00R 110.2(5) . . ?
C00G N007 C00L 117.7(4) . . ?
C00F N008 H008 125.3 . . ?
C00Y N008 H008 125.3 . . ?
C00Y N008 C00F 109.4(4) . . ?
C00O N009 H009 125.3 . . ?
C00Z N009 H009 125.3 . . ?
C00Z N009 C00O 109.5(5) . . ?
C00P N00A C00E 119.1(5) . . ?
C00J N00B H00B 130(4) . . ?
C016 N00B C00J 109.5(5) . . ?
C016 N00B H00B 120(4) . . ?
C00H C00C C00J 117.7(5) . . ?
C00H C00C C010 135.0(5) . . ?
C00J C00C C010 107.1(5) . . ?
C00F C00D C00K 117.0(5) . . ?
C00F C00D C00N 106.2(5) . . ?
C00K C00D C00N 136.8(5) . . ?
N00A C00E C00K 122.5(5) . . ?
N00A C00E C00M 116.6(5) . . ?
C00M C00E C00K 120.9(5) . . ?
N008 C00F C00D 108.3(5) . . ?
N008 C00F C00P 129.1(5) . . ?
C00D C00F C00P 122.6(5) . . ?
N007 C00G C00J 122.3(5) . . ?
N007 C00G C00O 117.5(5) . . ?
C00J C00G C00O 120.3(5) . . ?
C00C C00H C00T 124.8(5) . . ?
C00L C00H C00C 117.5(5) . . ?
C00L C00H C00T 117.6(5) . . ?
C00U C00I H00I 120.1 . . ?
C011 C00I H00I 120.1 . . ?
C011 C00I C00U 119.7(5) . . ?
N00B C00J C00C 107.0(5) . . ?
N00B C00J C00G 131.8(5) . . ?
C00G C00J C00C 121.1(5) . . ?
C00D C00K C011 125.0(5) . . ?
C00E C00K C00D 118.1(5) . . ?
C00E C00K C011 116.9(5) . . ?
N007 C00L C00S 115.1(5) . . ?
C00H C00L N007 123.3(5) . . ?
C00H C00L C00S 121.6(5) . . ?
C00E C00M H00M 115(3) . . ?
C00U C00M C00E 118.8(5) . . ?
C00U C00M H00M 126(3) . . ?
C00D C00N H00N 126.4 . . ?
C00Y C00N C00D 107.3(5) . . ?
C00Y C00N H00N 126.4 . . ?
N009 C00O C00G 121.1(5) . . ?
N009 C00O C00X 107.7(5) . . ?
C00X C00O C00G 130.9(5) . . ?
N00A C00P C00F 120.7(5) . . ?
N00A C00P C00R 118.1(5) . . ?
C00F C00P C00R 121.2(5) . . ?
O001 C00Q C014 112.4(5) . . ?
C00S C00Q O001 124.7(5) . . ?
C00S C00Q C014 122.8(5) . . ?
N006 C00R C00P 122.3(5) . . ?
N006 C00R C00V 107.4(5) . . ?
C00V C00R C00P 130.2(5) . . ?
C00L C00S H00S 121.3 . . ?
C00Q C00S C00L 117.4(5) . . ?
C00Q C00S H00S 121.3 . . ?
O002 C00T C00H 113.5(5) . . ?
C014 C00T O002 125.3(5) . . ?
C014 C00T C00H 121.2(5) . . ?
O005 C00U C00I 114.1(5) . . ?
C00M C00U O005 124.2(5) . . ?
C00M C00U C00I 121.7(6) . . ?
C00R C00V H00V 126.5 . . ?
C00R C00V C012 107.0(5) . . ?
C012 C00V H00V 126.5 . . ?
O001 C00W H00A 109.5 . . ?
O001 C00W H00C 109.5 . . ?
O001 C00W H00D 109.5 . . ?
H00A C00W H00C 109.5 . . ?
H00A C00W H00D 109.5 . . ?
H00C C00W H00D 109.5 . . ?
C00O C00X H00X 126.4 . . ?
C00O C00X C015 107.1(5) . . ?
C015 C00X H00X 126.4 . . ?
N008 C00Y C00N 108.9(5) . . ?
N008 C00Y H00Y 125.5 . . ?
C00N C00Y H00Y 125.5 . . ?
N009 C00Z H00Z 125.6 . . ?
N009 C00Z C015 108.8(5) . . ?
C015 C00Z H00Z 125.6 . . ?
C00C C010 H010 126.8 . . ?
C016 C010 C00C 106.4(5) . . ?
C016 C010 H010 126.8 . . ?
O003 C011 C00K 114.3(5) . . ?
C00I C011 O003 123.8(5) . . ?
C00I C011 C00K 121.9(6) . . ?
C00V C012 H012 125.9 . . ?
C013 C012 C00V 108.2(5) . . ?
C013 C012 H012 125.9 . . ?
N006 C013 C012 107.1(5) . . ?
N006 C013 H013 126.4 . . ?
C012 C013 H013 126.4 . . ?
C00Q C014 H014 120.4 . . ?
C00T C014 C00Q 119.1(5) . . ?
C00T C014 H014 120.4 . . ?
C00X C015 H015 126.6 . . ?
C00Z C015 C00X 106.9(5) . . ?
C00Z C015 H015 126.6 . . ?
N00B C016 C010 109.9(5) . . ?
N00B C016 H016 125.1 . . ?
C010 C016 H016 125.1 . . ?
O002 C017 H01A 109.5 . . ?
O002 C017 H01B 109.5 . . ?
O002 C017 H01C 109.5 . . ?
H01A C017 H01B 109.5 . . ?
H01A C017 H01C 109.5 . . ?
H01B C017 H01C 109.5 . . ?
O005 C018 H01D 109.5 . . ?
O005 C018 H01E 109.5 . . ?
O005 C018 H01F 109.5 . . ?
H01D C018 H01E 109.5 . . ?
H01D C018 H01F 109.5 . . ?
H01E C018 H01F 109.5 . . ?
O003 C019 H01G 109.5 . . ?
O003 C019 H01H 109.5 . . ?
O003 C019 H01I 109.5 . . ?
H01G C019 H01H 109.5 . . ?
H01G C019 H01I 109.5 . . ?
H01H C019 H01I 109.5 . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_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
-4 5 15 0.0351 -4.1301 4.8428 15.3579 -0.2677 0.9026 0.3372
-1 26 11 0.0295 -1.3175 25.6827 10.6031 -0.7935 0.6085 -0.0090
-10 15 10 0.0295 -10.4280 14.8197 9.7956 -0.6104 0.4680 0.6390
-6 -26 -8 0.0303 -6.3751 -25.8349 -7.7369 0.6767 -0.5190 0.5222
-1 -26 -10 0.0280 -0.5020 -26.4034 -10.1945 0.7865 -0.6032 0.1330
-3 31 7 0.0226 -3.4138 30.5238 6.6844 -0.9406 0.3328 0.0677
15 7 -3 0.0191 14.5956 7.3609 -2.5967 0.0086 -0.0029 -1.0000
-4 32 -3 0.0261 -4.4449 32.2377 -2.9720 -0.9572 -0.2838 0.0575
0 -34 4 0.0231 0.1076 -33.6116 3.6297 0.9322 0.2764 0.2337
-13 9 -6 0.0344 -13.1851 8.7250 -5.7601 -0.4027 -0.5251 0.7497
-2 -23 12 0.0313 -1.7664 -23.1457 11.7519 0.5720 0.7458 0.3413
1 -23 12 0.0334 0.9633 -22.8097 11.8410 0.6002 0.7826 0.1649
1 23 -12 0.0346 1.2689 23.1418 -11.7977 -0.5786 -0.7545 -0.3097
-15 -7 -1 0.0357 -14.5859 -6.7428 -1.4658 -0.0065 -0.2512 0.9679
-1 -8 -15 0.0381 -0.7024 -7.8116 -15.4263 0.2843 -0.9587 -0.0090
-2 -32 -6 0.0236 -1.8289 -32.0002 -5.5306 0.9035 -0.3197 0.2855
-3 -34 -1 0.0225 -2.5394 -33.9741 -0.7021 0.9262 -0.0240 0.3763
-5 32 2 0.0228 -5.4824 31.8970 2.1754 -0.9866 0.0256 0.1609
0 34 -4 0.0252 0.3950 33.5851 -3.6866 -0.9242 -0.2740 -0.2661

_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_mf004
_database_code_depnum_ccdc_archive 'CCDC 1896806'
loop_
_audit_author_name
_audit_author_address
'Milosz Pawlicki'
;Department of Chemistry University of Wroclaw
Poland
;
_audit_update_record             
;
2019-02-12 deposited with the CCDC.	2019-04-25 downloaded from the CCDC.
;
_audit_creation_date             2018-12-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 B F2 N3 O2'
_chemical_formula_sum            'C17.14 H14.50 B F2 N3 O2'
_chemical_formula_weight         343.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.1306(3)
_cell_length_b                   11.7622(3)
_cell_length_c                   24.0194(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.217(2)
_cell_angle_gamma                90
_cell_volume                     3143.92(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8060
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8775
_cell_measurement_theta_min      3.0160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1419
_exptl_crystal_size_max          0.829
_exptl_crystal_size_mid          0.548
_exptl_crystal_size_min          0.366
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20535
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_min         3.016
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.3359
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -54.00   60.75   0.7500   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -79.0000    0.0000 153

#__ type_ start__ end____ width___ exp.time_
  2 omega  -54.00   60.75   0.7500   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -79.0000   90.0000 153

#__ type_ start__ end____ width___ exp.time_
  3 omega  -54.00   60.75   0.7500   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -79.0000  180.0000 153

#__ type_ start__ end____ width___ exp.time_
  4 omega  -54.00   60.75   0.7500   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -79.0000  270.0000 153
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0024937000
_diffrn_orient_matrix_UB_12      -0.0343354000
_diffrn_orient_matrix_UB_13      -0.0242852000
_diffrn_orient_matrix_UB_21      -0.0634537000
_diffrn_orient_matrix_UB_22      -0.0028337000
_diffrn_orient_matrix_UB_23      0.0017589000
_diffrn_orient_matrix_UB_31      -0.0054430000
_diffrn_orient_matrix_UB_32      0.0495313000
_diffrn_orient_matrix_UB_33      -0.0166961000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5157
_reflns_number_total             6900
_reflns_odcompleteness_completeness 99.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         6900
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0599
_refine_ls_restrained_S_all      1.043
_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)+(0.0863P)²+1.5087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1730
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H007(0.027) H009(0.03) H00O(0.029) H00P(0.028) H00Q(0.031)
 H00R(0.032) H00S(0.029) H00U(0.032) H00V(0.03) H00W(0.033) H00X(0.03)
 H00Y(0.03) H00Z(0.035) H010(0.035) H012(0.037) H013(0.045) H014(0.041)
 H015(0.042) H01D(0.05) H01E(0.05) H01F(0.05) H017(0.047) H019(0.044)
 H01G(0.052) H01H(0.052) H01I(0.052) H01A(0.142) H01B(0.142) H01C(0.142)
 H00A(0.054) H00B(0.054) H00C(0.054) H0AA(0.052) H0AB(0.052) H0AC(0.052)
 Fixed X: H007(0.838323) H009(0.562977) H00O(0.588494) H00P(0.768367)
 H00Q(0.477443) H00R(0.528055) H00S(0.463786) H00U(0.436467) H00V(0.706881)
 H00W(0.732406) H00X(0.764435) H00Y(0.958662) H00Z(0.801515) H010(0.741593)
 H012(0.985278) H013(1.016083) H014(0.879472) H015(0.844897) H01D(0.412475)
 H01E(0.387913) H01F(0.52032) H017(1.068843) H019(0.815632) H01G(0.792292)
 H01H(0.659754) H01I(0.76709) H01A(0.679549) H01B(0.799196) H01C(0.674973)
 H00A(0.90203) H00B(1.03552) H00C(1.007683) H0AA(1.108557) H0AB(1.081408)
 H0AC(1.004974)
 Fixed Y: H007(0.460389) H009(0.580521) H00O(0.34223) H00P(0.358896)
 H00Q(0.649576) H00R(0.471951) H00S(0.340785) H00U(0.646751) H00V(0.577031)
 H00W(0.319801) H00X(0.328399) H00Y(0.458676) H00Z(0.487826) H010(0.713035)
 H012(0.759851) H013(0.877761) H014(0.171769) H015(0.695334) H01D(0.238935)
 H01E(0.120047) H01F(0.161794) H017(0.91768) H019(0.161551) H01G(0.51775)
 H01H(0.474333) H01I(0.396068) H01A(0.81506) H01B(0.879168) H01C(0.936989)
 H00A(0.531812) H00B(0.489834) H00C(0.617236) H0AA(0.455558) H0AB(0.431623)
 H0AC(0.371835)
 Fixed Z: H007(0.401693) H009(0.180228) H00O(-0.021109) H00P(0.471267)
 H00Q(0.261532) H00R(0.402533) H00S(0.135687) H00U(0.362969) H00V(0.090734)
 H00W(0.571946) H00X(0.146525) H00Y(0.313387) H00Z(0.625142) H010(0.362698)
 H012(0.384106) H013(0.54001) H014(0.192718) H015(0.202415) H01D(-0.035645)
 H01E(-0.008668) H01F(-0.016242) H017(0.442842) H019(0.290248) H01G(-0.085213)
 H01H(-0.080416) H01I(-0.061527) H01A(0.191734) H01B(0.207107) H01C(0.217961)
 H00A(0.144082) H00B(0.141885) H00C(0.155795) H0AA(0.240676) H0AB(0.177447)
 H0AC(0.223048)
;
_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
F001 F 0.55230(12) 0.23268(10) 0.33747(5) 0.0329(3) Uani 1 1 d . . . . .
F002 F 0.72312(12) 0.31092(10) 0.37363(5) 0.0344(3) Uani 1 1 d . . . . .
F003 F 0.80263(12) 0.74102(11) 0.59159(5) 0.0366(3) Uani 1 1 d . . . . .
F004 F 0.99149(12) 0.67356(11) 0.60480(6) 0.0421(4) Uani 1 1 d . . . . .
O005 O 0.43854(13) 0.23700(12) 0.04589(6) 0.0288(3) Uani 1 1 d . . . . .
O006 O 0.73351(14) 0.51921(13) -0.00831(6) 0.0314(4) Uani 1 1 d . . . . .
N007 N 0.85225(14) 0.53227(14) 0.40071(7) 0.0226(4) Uani 1 1 d . . . . .
H007 H 0.838323 0.460389 0.401693 0.027 Uiso 1 1 calc R . . . .
N008 N 0.58427(15) 0.43473(14) 0.32417(7) 0.0226(4) Uani 1 1 d . . . . .
N009 N 0.58378(16) 0.51049(14) 0.17683(7) 0.0253(4) Uani 1 1 d . . . . .
H009 H 0.562977 0.580521 0.180228 0.030 Uiso 1 1 calc R . . . .
N00A N 0.84946(15) 0.55857(14) 0.55146(7) 0.0237(4) Uani 1 1 d . . . . .
N00B N 0.70426(15) 0.29488(14) 0.27367(7) 0.0248(4) Uani 1 1 d . . . . .
N00C N 0.93400(15) 0.73422(14) 0.51230(8) 0.0278(4) Uani 1 1 d . . . . .
O00D O 0.71693(16) 0.81678(17) 0.27265(8) 0.0526(6) Uani 1 1 d . . . . .
O00E O 0.97892(19) 0.51562(19) 0.21209(8) 0.0579(6) Uani 1 1 d D . . . .
C00F C 0.83724(17) 0.51539(17) 0.49786(8) 0.0208(4) Uani 1 1 d . . . . .
C00G C 0.87008(16) 0.58154(16) 0.45029(8) 0.0204(4) Uani 1 1 d . . . . .
C00H C 0.61078(17) 0.45280(16) 0.22368(8) 0.0212(4) Uani 1 1 d . . . . .
C00I C 0.56672(18) 0.49512(16) 0.27503(8) 0.0217(4) Uani 1 1 d . . . . .
C00J C 0.68436(17) 0.35376(16) 0.22391(8) 0.0220(4) Uani 1 1 d . . . . .
C00K C 0.51382(17) 0.32712(16) 0.05525(8) 0.0223(4) Uani 1 1 d . . . . .
C00L C 0.92173(17) 0.69157(17) 0.45838(9) 0.0241(4) Uani 1 1 d . . . . .
C00M C 0.85288(18) 0.58119(18) 0.34634(9) 0.0241(4) Uani 1 1 d . . . . .
C00N C 0.58690(19) 0.46438(16) 0.12140(8) 0.0233(4) Uani 1 1 d . . . . .
C00O C 0.58731(17) 0.37327(17) 0.01449(9) 0.0238(4) Uani 1 1 d . . . . .
H00O H 0.588494 0.342230 -0.021109 0.029 Uiso 1 1 calc R . . . .
C00P C 0.78588(17) 0.40722(17) 0.50099(9) 0.0230(4) Uani 1 1 d . . . . .
H00P H 0.768367 0.358896 0.471267 0.028 Uiso 1 1 calc R . . . .
C00Q C 0.50121(18) 0.59367(17) 0.28683(9) 0.0260(4) Uani 1 1 d . . . . .
H00Q H 0.477443 0.649576 0.261532 0.031 Uiso 1 1 calc R . . . .
C00R C 0.53017(19) 0.49387(18) 0.36536(9) 0.0264(5) Uani 1 1 d . . . . .
H00R H 0.528055 0.471951 0.402533 0.032 Uiso 1 1 calc R . . . .
C00S C 0.51287(18) 0.37192(17) 0.10879(9) 0.0240(4) Uani 1 1 d . . . . .
H00S H 0.463786 0.340785 0.135687 0.029 Uiso 1 1 calc R . . . .
C00T C 0.65894(18) 0.46706(17) 0.02843(9) 0.0245(4) Uani 1 1 d . . . . .
C00U C 0.47856(19) 0.59205(17) 0.34335(9) 0.0269(5) Uani 1 1 d . . . . .
H00U H 0.436467 0.646751 0.362969 0.032 Uiso 1 1 calc R . . . .
C00V C 0.65943(18) 0.51422(17) 0.08191(9) 0.0252(4) Uani 1 1 d . . . . .
H00V H 0.706881 0.577031 0.090734 0.030 Uiso 1 1 calc R . . . .
C00W C 0.76583(19) 0.38539(18) 0.55718(9) 0.0272(5) Uani 1 1 d . . . . .
H00W H 0.732406 0.319801 0.571946 0.033 Uiso 1 1 calc R . . . .
C00X C 0.75901(18) 0.30577(17) 0.18349(9) 0.0248(4) Uani 1 1 d . . . . .
H00X H 0.764435 0.328399 0.146525 0.030 Uiso 1 1 calc R . . . .
C00Y C 0.91575(18) 0.52464(18) 0.30519(9) 0.0251(4) Uani 1 1 d . . . . .
H00Y H 0.958662 0.458676 0.313387 0.030 Uiso 1 1 calc R . . . .
C00Z C 0.80505(19) 0.47967(19) 0.58670(9) 0.0294(5) Uani 1 1 d . . . . .
H00Z H 0.801515 0.487826 0.625142 0.035 Uiso 1 1 calc R . . . .
C010 C 0.78514(18) 0.67782(19) 0.33494(9) 0.0292(5) Uani 1 1 d . . . . .
H010 H 0.741593 0.713035 0.362698 0.035 Uiso 1 1 calc R . . . .
C011 C 0.91289(19) 0.5690(2) 0.25167(9) 0.0297(5) Uani 1 1 d . . . . .
C012 C 0.97929(18) 0.76712(18) 0.42250(11) 0.0312(5) Uani 1 1 d . . . . .
H012 H 0.985278 0.759851 0.384106 0.037 Uiso 1 1 calc R . . . .
C013 C 0.9961(2) 0.83210(19) 0.50959(12) 0.0373(6) Uani 1 1 d . . . . .
H013 H 1.016083 0.877761 0.540010 0.045 Uiso 1 1 calc R . . . .
C014 C 0.8229(2) 0.2184(2) 0.20922(10) 0.0343(5) Uani 1 1 d . . . . .
H014 H 0.879472 0.171769 0.192718 0.041 Uiso 1 1 calc R . . . .
C015 C 0.84699(19) 0.6667(2) 0.23851(9) 0.0347(5) Uani 1 1 d . . . . .
H015 H 0.844897 0.695334 0.202415 0.042 Uiso 1 1 calc R . . . .
C016 C 0.4399(2) 0.1852(2) -0.00813(10) 0.0331(5) Uani 1 1 d . . . . .
H01D H 0.412475 0.238935 -0.035645 0.050 Uiso 1 1 calc GR . . . .
H01E H 0.387913 0.120047 -0.008668 0.050 Uiso 1 1 calc GR . . . .
H01F H 0.520320 0.161794 -0.016242 0.050 Uiso 1 1 calc GR . . . .
C017 C 1.0258(2) 0.85516(19) 0.45526(12) 0.0393(6) Uani 1 1 d . . . . .
H017 H 1.068843 0.917680 0.442842 0.047 Uiso 1 1 calc R . . . .
C018 C 0.78399(19) 0.7206(2) 0.28102(10) 0.0347(5) Uani 1 1 d . . . . .
C019 C 0.7870(2) 0.2134(2) 0.26393(10) 0.0367(6) Uani 1 1 d . . . . .
H019 H 0.815632 0.161551 0.290248 0.044 Uiso 1 1 calc R . . . .
C01A C 0.7386(2) 0.4730(2) -0.06341(9) 0.0346(5) Uani 1 1 d . . . . .
H01G H 0.792292 0.517750 -0.085213 0.052 Uiso 1 1 calc GR . . . .
H01H H 0.659754 0.474333 -0.080416 0.052 Uiso 1 1 calc GR . . . .
H01I H 0.767090 0.396068 -0.061527 0.052 Uiso 1 1 calc GR . . . .
B01B B 0.6412(2) 0.31632(19) 0.32886(10) 0.0252(5) Uani 1 1 d . . . . .
B01C B 0.8938(2) 0.6782(2) 0.56702(11) 0.0286(5) Uani 1 1 d . . . . .
C01D C 0.7177(3) 0.8661(4) 0.21779(15) 0.0945(16) Uani 1 1 d . . . A 3
H01A H 0.679549 0.815060 0.191734 0.142 Uiso 1 1 calc GR . . A 3
H01B H 0.799196 0.879168 0.207107 0.142 Uiso 1 1 calc GR . . A 3
H01C H 0.674973 0.936989 0.217961 0.142 Uiso 1 1 calc GR . . A 3
C00E C 0.9812(4) 0.5402(4) 0.16022(15) 0.0361(11) Uani 0.598(6) 1 d D . P B 1
H00A H 0.902030 0.531812 0.144082 0.054 Uiso 0.598(6) 1 calc GR . P B 1
H00B H 1.035520 0.489834 0.141885 0.054 Uiso 0.598(6) 1 calc GR . P B 1
H00C H 1.007683 0.617236 0.155795 0.054 Uiso 0.598(6) 1 calc GR . P B 1
C0AA C 1.0464(5) 0.4404(5) 0.2134(2) 0.0347(16) Uani 0.402(6) 1 d . . P B 2
H0AA H 1.108557 0.455558 0.240676 0.052 Uiso 0.402(6) 1 calc GR . P B 2
H0AB H 1.081408 0.431623 0.177447 0.052 Uiso 0.402(6) 1 calc GR . P B 2
H0AC H 1.004974 0.371835 0.223048 0.052 Uiso 0.402(6) 1 calc GR . P B 2


_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
F001 B01B 1.414(3) . ?
F002 B01B 1.397(3) . ?
F003 B01C 1.396(3) . ?
F004 B01C 1.403(3) . ?
O005 C00K 1.367(2) . ?
O005 C016 1.434(3) . ?
O006 C00T 1.369(2) . ?
O006 C01A 1.433(3) . ?
N007 H007 0.8600 . ?
N007 C00G 1.335(3) . ?
N007 C00M 1.427(3) . ?
N008 C00I 1.388(2) . ?
N008 C00R 1.361(3) . ?
N008 B01B 1.533(3) . ?
N009 H009 0.8600 . ?
N009 C00H 1.343(2) . ?
N009 C00N 1.439(3) . ?
N00A C00F 1.388(3) . ?
N00A C00Z 1.356(3) . ?
N00A B01C 1.535(3) . ?
N00B C00J 1.395(3) . ?
N00B C019 1.353(3) . ?
N00B B01B 1.534(3) . ?
N00C C00L 1.393(3) . ?
N00C C013 1.345(3) . ?
N00C B01C 1.545(3) . ?
O00D C018 1.368(3) . ?
O00D C01D 1.440(3) . ?
O00E C011 1.367(3) . ?
O00E C00E 1.280(4) . ?
O00E C0AA 1.160(6) . ?
C00F C00G 1.436(3) . ?
C00F C00P 1.398(3) . ?
C00G C00L 1.428(3) . ?
C00H C00I 1.427(3) . ?
C00H C00J 1.424(3) . ?
C00I C00Q 1.402(3) . ?
C00J C00X 1.409(3) . ?
C00K C00O 1.399(3) . ?
C00K C00S 1.390(3) . ?
C00L C012 1.402(3) . ?
C00M C00Y 1.392(3) . ?
C00M C010 1.388(3) . ?
C00N C00S 1.394(3) . ?
C00N C00V 1.388(3) . ?
C00O H00O 0.9300 . ?
C00O C00T 1.398(3) . ?
C00P H00P 0.9300 . ?
C00P C00W 1.396(3) . ?
C00Q H00Q 0.9300 . ?
C00Q C00U 1.386(3) . ?
C00R H00R 0.9300 . ?
C00R C00U 1.389(3) . ?
C00S H00S 0.9300 . ?
C00T C00V 1.399(3) . ?
C00U H00U 0.9300 . ?
C00V H00V 0.9300 . ?
C00W H00W 0.9300 . ?
C00W C00Z 1.382(3) . ?
C00X H00X 0.9300 . ?
C00X C014 1.388(3) . ?
C00Y H00Y 0.9300 . ?
C00Y C011 1.387(3) . ?
C00Z H00Z 0.9300 . ?
C010 H010 0.9300 . ?
C010 C018 1.389(3) . ?
C011 C015 1.396(3) . ?
C012 H012 0.9300 . ?
C012 C017 1.394(3) . ?
C013 H013 0.9300 . ?
C013 C017 1.380(4) . ?
C014 H014 0.9300 . ?
C014 C019 1.383(3) . ?
C015 H015 0.9300 . ?
C015 C018 1.403(3) . ?
C016 H01D 0.9600 . ?
C016 H01E 0.9600 . ?
C016 H01F 0.9600 . ?
C017 H017 0.9300 . ?
C019 H019 0.9300 . ?
C01A H01G 0.9600 . ?
C01A H01H 0.9600 . ?
C01A H01I 0.9600 . ?
C01D H01A 0.9600 . ?
C01D H01B 0.9600 . ?
C01D H01C 0.9600 . ?
C00E H00A 0.9600 . ?
C00E H00B 0.9600 . ?
C00E H00C 0.9600 . ?
C0AA H0AA 0.9600 . ?
C0AA H0AB 0.9600 . ?
C0AA H0AC 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
C00K O005 C016 117.41(16) . . ?
C00T O006 C01A 117.50(17) . . ?
C00G N007 H007 115.2 . . ?
C00G N007 C00M 129.60(17) . . ?
C00M N007 H007 115.2 . . ?
C00I N008 B01B 125.31(17) . . ?
C00R N008 C00I 107.48(17) . . ?
C00R N008 B01B 126.84(17) . . ?
C00H N009 H009 117.4 . . ?
C00H N009 C00N 125.15(17) . . ?
C00N N009 H009 117.4 . . ?
C00F N00A B01C 125.87(18) . . ?
C00Z N00A C00F 107.38(17) . . ?
C00Z N00A B01C 126.51(18) . . ?
C00J N00B B01B 126.27(17) . . ?
C019 N00B C00J 107.43(18) . . ?
C019 N00B B01B 126.28(18) . . ?
C00L N00C B01C 127.82(17) . . ?
C013 N00C C00L 107.7(2) . . ?
C013 N00C B01C 124.4(2) . . ?
C018 O00D C01D 117.0(2) . . ?
C00E O00E C011 126.6(3) . . ?
C0AA O00E C011 133.6(4) . . ?
N00A C00F C00G 121.21(18) . . ?
N00A C00F C00P 108.38(17) . . ?
C00P C00F C00G 130.35(19) . . ?
N007 C00G C00F 116.03(18) . . ?
N007 C00G C00L 124.51(18) . . ?
C00L C00G C00F 119.43(18) . . ?
N009 C00H C00I 118.25(17) . . ?
N009 C00H C00J 122.35(18) . . ?
C00J C00H C00I 119.37(17) . . ?
N008 C00I C00H 120.79(17) . . ?
N008 C00I C00Q 108.41(17) . . ?
C00Q C00I C00H 130.79(19) . . ?
N00B C00J C00H 119.35(17) . . ?
N00B C00J C00X 107.84(17) . . ?
C00X C00J C00H 132.26(19) . . ?
O005 C00K C00O 123.46(18) . . ?
O005 C00K C00S 115.43(18) . . ?
C00S C00K C00O 121.10(18) . . ?
N00C C00L C00G 118.96(18) . . ?
N00C C00L C012 107.83(18) . . ?
C012 C00L C00G 132.7(2) . . ?
C00Y C00M N007 117.99(18) . . ?
C010 C00M N007 119.84(18) . . ?
C010 C00M C00Y 122.0(2) . . ?
C00S C00N N009 118.00(18) . . ?
C00V C00N N009 119.93(18) . . ?
C00V C00N C00S 122.04(19) . . ?
C00K C00O H00O 120.7 . . ?
C00T C00O C00K 118.53(19) . . ?
C00T C00O H00O 120.7 . . ?
C00F C00P H00P 126.5 . . ?
C00F C00P C00W 107.06(18) . . ?
C00W C00P H00P 126.5 . . ?
C00I C00Q H00Q 126.5 . . ?
C00U C00Q C00I 107.03(18) . . ?
C00U C00Q H00Q 126.5 . . ?
N008 C00R H00R 125.2 . . ?
N008 C00R C00U 109.51(18) . . ?
C00U C00R H00R 125.2 . . ?
C00K C00S C00N 118.73(19) . . ?
C00K C00S H00S 120.6 . . ?
C00N C00S H00S 120.6 . . ?
O006 C00T C00O 123.34(19) . . ?
O006 C00T C00V 115.05(18) . . ?
C00O C00T C00V 121.61(19) . . ?
C00Q C00U C00R 107.57(18) . . ?
C00Q C00U H00U 126.2 . . ?
C00R C00U H00U 126.2 . . ?
C00N C00V C00T 117.96(19) . . ?
C00N C00V H00V 121.0 . . ?
C00T C00V H00V 121.0 . . ?
C00P C00W H00W 126.5 . . ?
C00Z C00W C00P 107.04(19) . . ?
C00Z C00W H00W 126.5 . . ?
C00J C00X H00X 126.5 . . ?
C014 C00X C00J 107.09(19) . . ?
C014 C00X H00X 126.5 . . ?
C00M C00Y H00Y 120.8 . . ?
C011 C00Y C00M 118.4(2) . . ?
C011 C00Y H00Y 120.8 . . ?
N00A C00Z C00W 110.14(19) . . ?
N00A C00Z H00Z 124.9 . . ?
C00W C00Z H00Z 124.9 . . ?
C00M C010 H010 120.8 . . ?
C00M C010 C018 118.4(2) . . ?
C018 C010 H010 120.8 . . ?
O00E C011 C00Y 118.0(2) . . ?
O00E C011 C015 120.6(2) . . ?
C00Y C011 C015 121.4(2) . . ?
C00L C012 H012 126.5 . . ?
C017 C012 C00L 107.0(2) . . ?
C017 C012 H012 126.5 . . ?
N00C C013 H013 124.8 . . ?
N00C C013 C017 110.4(2) . . ?
C017 C013 H013 124.8 . . ?
C00X C014 H014 126.3 . . ?
C019 C014 C00X 107.4(2) . . ?
C019 C014 H014 126.3 . . ?
C011 C015 H015 120.8 . . ?
C011 C015 C018 118.4(2) . . ?
C018 C015 H015 120.8 . . ?
O005 C016 H01D 109.5 . . ?
O005 C016 H01E 109.5 . . ?
O005 C016 H01F 109.5 . . ?
H01D C016 H01E 109.5 . . ?
H01D C016 H01F 109.5 . . ?
H01E C016 H01F 109.5 . . ?
C012 C017 H017 126.5 . . ?
C013 C017 C012 107.1(2) . . ?
C013 C017 H017 126.5 . . ?
O00D C018 C010 115.5(2) . . ?
O00D C018 C015 123.1(2) . . ?
C010 C018 C015 121.3(2) . . ?
N00B C019 C014 110.2(2) . . ?
N00B C019 H019 124.9 . . ?
C014 C019 H019 124.9 . . ?
O006 C01A H01G 109.5 . . ?
O006 C01A H01H 109.5 . . ?
O006 C01A H01I 109.5 . . ?
H01G C01A H01H 109.5 . . ?
H01G C01A H01I 109.5 . . ?
H01H C01A H01I 109.5 . . ?
F001 B01B N008 110.70(18) . . ?
F001 B01B N00B 110.28(17) . . ?
F002 B01B F001 107.65(17) . . ?
F002 B01B N008 111.10(17) . . ?
F002 B01B N00B 110.77(18) . . ?
N008 B01B N00B 106.37(16) . . ?
F003 B01C F004 107.94(18) . . ?
F003 B01C N00A 110.81(19) . . ?
F003 B01C N00C 111.13(18) . . ?
F004 B01C N00A 111.24(17) . . ?
F004 B01C N00C 109.42(19) . . ?
N00A B01C N00C 106.32(17) . . ?
O00D C01D H01A 109.5 . . ?
O00D C01D H01B 109.5 . . ?
O00D C01D H01C 109.5 . . ?
H01A C01D H01B 109.5 . . ?
H01A C01D H01C 109.5 . . ?
H01B C01D H01C 109.5 . . ?
O00E C00E H00A 109.5 . . ?
O00E C00E H00B 109.5 . . ?
O00E C00E H00C 109.5 . . ?
H00A C00E H00B 109.5 . . ?
H00A C00E H00C 109.5 . . ?
H00B C00E H00C 109.5 . . ?
O00E C0AA H0AA 109.5 . . ?
O00E C0AA H0AB 109.5 . . ?
O00E C0AA H0AC 109.5 . . ?
H0AA C0AA H0AB 109.5 . . ?
H0AA C0AA H0AC 109.5 . . ?
H0AB C0AA H0AC 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
