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

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

data_exp_6811
_database_code_depnum_ccdc_archive 'CCDC 1917599'
loop_
_audit_author_name
_audit_author_address
'Ya Wang'
;Huaqiao University
China
;
_audit_update_record             
;
2019-05-21 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;
_audit_creation_date             2019-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 N2 O2'
_chemical_formula_sum            'C13 H14 N2 O2'
_chemical_formula_weight         230.26
_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'
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        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.722(4)
_cell_length_b                   7.3514(16)
_cell_length_c                   20.934(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.85(2)
_cell_angle_gamma                90
_cell_volume                     2509.1(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1388
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8300
_cell_measurement_theta_min      3.9950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4649
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.481
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  51.00   1.00    7.50    --  -16.28  38.00  60.00   83
  2  ω    -14.00  31.00   1.00    7.50    --   15.49 -99.00 -30.00   45
  3  ω    -22.00  21.00   1.00    7.50    --  -16.28 -99.00  60.00   43
  4  ω    -23.00  23.00   1.00    7.50    --  -16.28 -99.00-150.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0418124000
_diffrn_orient_matrix_UB_12      -0.0185763000
_diffrn_orient_matrix_UB_13      -0.0141698000
_diffrn_orient_matrix_UB_21      -0.0120342000
_diffrn_orient_matrix_UB_22      0.0638675000
_diffrn_orient_matrix_UB_23      0.0215082000
_diffrn_orient_matrix_UB_31      0.0000101000
_diffrn_orient_matrix_UB_32      0.0701657000
_diffrn_orient_matrix_UB_33      -0.0231996000
_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                1614
_reflns_number_total             2199
_reflns_odcompleteness_completeness 99.42
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.004
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1543
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00F(H00C,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E)
2.c Idealised Me refined as rotating group:
 C00G(H00G,H00H,H00I), C00H(H00J,H00K,H00L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.59961(8) -0.20071(16) 0.35785(6) 0.0562(4) Uani 1 1 d . . . . .
N002 N 0.46063(8) 0.31798(18) 0.36373(6) 0.0462(4) Uani 1 1 d . . . . .
O003 O 0.57671(10) -0.15375(19) 0.45728(7) 0.0812(5) Uani 1 1 d . . . . .
N004 N 0.52157(10) 0.1158(2) 0.31118(7) 0.0618(5) Uani 1 1 d . . . . .
C005 C 0.41684(10) 0.4785(2) 0.37510(8) 0.0458(4) Uani 1 1 d . . . . .
C006 C 0.52848(10) 0.0618(2) 0.37449(7) 0.0457(4) Uani 1 1 d . . . . .
C007 C 0.56994(10) -0.1061(2) 0.40166(8) 0.0505(5) Uani 1 1 d . . . . .
C008 C 0.49184(10) 0.1834(2) 0.40719(8) 0.0505(5) Uani 1 1 d . . . . .
H008 H 0.4885 0.1767 0.4509 0.061 Uiso 1 1 calc R . . . .
C009 C 0.48064(13) 0.2693(3) 0.30679(8) 0.0641(6) Uani 1 1 d . . . . .
H009 H 0.4668 0.3377 0.2686 0.077 Uiso 1 1 calc R . . . .
C00A C 0.39701(13) 0.6104(3) 0.32745(10) 0.0651(6) Uani 1 1 d . . . . .
H00A H 0.4117 0.5956 0.2874 0.078 Uiso 1 1 calc R . . . .
C00B C 0.39444(12) 0.5035(3) 0.43391(9) 0.0638(6) Uani 1 1 d . . . . .
H00B H 0.4073 0.4158 0.4666 0.077 Uiso 1 1 calc R . . . .
C00C C 0.33222(12) 0.7930(3) 0.39693(11) 0.0629(6) Uani 1 1 d . . . . .
C00D C 0.35263(12) 0.6596(3) 0.44420(10) 0.0701(6) Uani 1 1 d . . . . .
H00D H 0.3378 0.6750 0.4841 0.084 Uiso 1 1 calc R . . . .
C00E C 0.35533(13) 0.7643(3) 0.33919(11) 0.0705(6) Uani 1 1 d . . . . .
H00E H 0.3425 0.8520 0.3065 0.085 Uiso 1 1 calc R . . . .
C00F C 0.64311(13) -0.3674(3) 0.38120(11) 0.0725(6) Uani 1 1 d . . . . .
H00C H 0.6068 -0.4512 0.3967 0.087 Uiso 1 1 calc R . . . .
H00F H 0.6893 -0.3411 0.4171 0.087 Uiso 1 1 calc R . . . .
C00G C 0.28522(16) 0.9618(3) 0.40768(14) 0.0906(8) Uani 1 1 d . . . . .
H00G H 0.2364 0.9273 0.4215 0.136 Uiso 1 1 calc GR . . . .
H00H H 0.2706 1.0293 0.3675 0.136 Uiso 1 1 calc GR . . . .
H00I H 0.3189 1.0360 0.4408 0.136 Uiso 1 1 calc GR . . . .
C00H C 0.67209(16) -0.4486(4) 0.32567(13) 0.1076(10) Uani 1 1 d . . . . .
H00J H 0.6258 -0.4772 0.2909 0.161 Uiso 1 1 calc GR . . . .
H00K H 0.7023 -0.5578 0.3400 0.161 Uiso 1 1 calc GR . . . .
H00L H 0.7069 -0.3636 0.3101 0.161 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
O001 C007 1.332(2) . ?
O001 C00F 1.453(2) . ?
N002 C005 1.436(2) . ?
N002 C008 1.367(2) . ?
N002 C009 1.356(2) . ?
O003 C007 1.197(2) . ?
N004 C006 1.363(2) . ?
N004 C009 1.312(2) . ?
C005 C00A 1.378(2) . ?
C005 C00B 1.377(2) . ?
C006 C007 1.467(2) . ?
C006 C008 1.353(2) . ?
C008 H008 0.9300 . ?
C009 H009 0.9300 . ?
C00A H00A 0.9300 . ?
C00A C00E 1.380(3) . ?
C00B H00B 0.9300 . ?
C00B C00D 1.385(3) . ?
C00C C00D 1.381(3) . ?
C00C C00E 1.365(3) . ?
C00C C00G 1.512(3) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00F H00C 0.9700 . ?
C00F H00F 0.9700 . ?
C00F C00H 1.481(3) . ?
C00G H00G 0.9600 . ?
C00G H00H 0.9600 . ?
C00G H00I 0.9600 . ?
C00H H00J 0.9600 . ?
C00H H00K 0.9600 . ?
C00H H00L 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
C007 O001 C00F 116.36(14) . . ?
C008 N002 C005 128.15(13) . . ?
C009 N002 C005 126.66(15) . . ?
C009 N002 C008 105.19(14) . . ?
C009 N004 C006 104.39(14) . . ?
C00A C005 N002 120.51(15) . . ?
C00B C005 N002 120.52(15) . . ?
C00B C005 C00A 118.96(17) . . ?
N004 C006 C007 123.53(14) . . ?
C008 C006 N004 110.46(15) . . ?
C008 C006 C007 126.01(15) . . ?
O001 C007 C006 112.88(14) . . ?
O003 C007 O001 123.22(17) . . ?
O003 C007 C006 123.90(16) . . ?
N002 C008 H008 126.6 . . ?
C006 C008 N002 106.87(14) . . ?
C006 C008 H008 126.6 . . ?
N002 C009 H009 123.5 . . ?
N004 C009 N002 113.08(16) . . ?
N004 C009 H009 123.5 . . ?
C005 C00A H00A 120.1 . . ?
C005 C00A C00E 119.88(17) . . ?
C00E C00A H00A 120.1 . . ?
C005 C00B H00B 120.1 . . ?
C005 C00B C00D 119.78(18) . . ?
C00D C00B H00B 120.1 . . ?
C00D C00C C00G 122.0(2) . . ?
C00E C00C C00D 116.81(18) . . ?
C00E C00C C00G 121.2(2) . . ?
C00B C00D H00D 119.0 . . ?
C00C C00D C00B 122.00(18) . . ?
C00C C00D H00D 119.0 . . ?
C00A C00E H00E 118.7 . . ?
C00C C00E C00A 122.57(19) . . ?
C00C C00E H00E 118.7 . . ?
O001 C00F H00C 110.2 . . ?
O001 C00F H00F 110.2 . . ?
O001 C00F C00H 107.62(18) . . ?
H00C C00F H00F 108.5 . . ?
C00H C00F H00C 110.2 . . ?
C00H C00F H00F 110.2 . . ?
C00C C00G H00G 109.5 . . ?
C00C C00G H00H 109.5 . . ?
C00C C00G H00I 109.5 . . ?
H00G C00G H00H 109.5 . . ?
H00G C00G H00I 109.5 . . ?
H00H C00G H00I 109.5 . . ?
C00F C00H H00J 109.5 . . ?
C00F C00H H00K 109.5 . . ?
C00F C00H H00L 109.5 . . ?
H00J C00H H00K 109.5 . . ?
H00J C00H H00L 109.5 . . ?
H00K C00H H00L 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_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 1.796
_oxdiff_exptl_absorpt_empirical_full_min 0.391
####################################################################### 
# 
# 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_exp_7025
_database_code_depnum_ccdc_archive 'CCDC 1937993'
loop_
_audit_author_name
_audit_author_address
'Ya Wang'
;Huaqiao University
China
;
_audit_update_record             
;
2019-07-03 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;
_audit_creation_date             2019-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H8 N4'
_chemical_formula_sum            'C8 H8 N4'
_chemical_formula_weight         160.18
_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'
N N 0.0061 0.0033 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.7747(9)
_cell_length_b                   5.6834(5)
_cell_length_c                   14.3307(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.261(9)
_cell_angle_gamma                90
_cell_volume                     791.37(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    948
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5660
_cell_measurement_theta_min      4.5500
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3418
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.142
_diffrn_reflns_theta_min         3.860
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  83.00   1.00    5.70    --   15.65  57.00 150.00   50
  2  ω     26.00  82.00   1.00    5.70    --   15.65  77.00 -90.00   56
  3  ω    -14.00  84.00   1.00    5.70    --   15.65  19.00  90.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0364810000
_diffrn_orient_matrix_UB_12      0.0843325000
_diffrn_orient_matrix_UB_13      0.0296007000
_diffrn_orient_matrix_UB_21      -0.0521910000
_diffrn_orient_matrix_UB_22      -0.0039698000
_diffrn_orient_matrix_UB_23      0.0306732000
_diffrn_orient_matrix_UB_31      0.0356960000
_diffrn_orient_matrix_UB_32      -0.0918392000
_diffrn_orient_matrix_UB_33      0.0257843000
_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                1174
_reflns_number_total             1834
_reflns_odcompleteness_completeness 99.16
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.154
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1834
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.037
_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)+(0.0713P)²+0.0353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1511
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.81100(17) 0.7570(3) 0.35260(11) 0.0779(5) Uani 1 1 d . . . . .
N2 N 0.75038(18) 0.5563(3) 0.37474(13) 0.0826(5) Uani 1 1 d . . . . .
N3 N 0.62342(17) 0.5905(3) 0.38487(12) 0.0789(5) Uani 1 1 d . . . . .
N4 N 0.59807(13) 0.8191(2) 0.36842(9) 0.0532(4) Uani 1 1 d . . . . .
C1 C 0.71516(17) 0.9151(3) 0.35010(12) 0.0677(5) Uani 1 1 d . . . . .
H1 H 0.727166 1.073650 0.337224 0.081 Uiso 1 1 calc R . . . .
C2 C 0.46532(15) 0.9187(3) 0.37333(10) 0.0500(4) Uani 1 1 d . . . . .
C3 C 0.37345(17) 0.8065(3) 0.42367(11) 0.0596(5) Uani 1 1 d . . . . .
H3 H 0.396951 0.665997 0.454596 0.072 Uiso 1 1 calc R . . . .
C4 C 0.24624(17) 0.9050(3) 0.42767(12) 0.0642(5) Uani 1 1 d . . . . .
H4 H 0.183129 0.827982 0.461027 0.077 Uiso 1 1 calc R . . . .
C5 C 0.20914(16) 1.1141(3) 0.38388(11) 0.0589(5) Uani 1 1 d . . . . .
C6 C 0.30417(18) 1.2218(3) 0.33356(12) 0.0606(5) Uani 1 1 d . . . . .
H6 H 0.281494 1.363437 0.303274 0.073 Uiso 1 1 calc R . . . .
C7 C 0.43128(16) 1.1248(3) 0.32717(11) 0.0557(4) Uani 1 1 d . . . . .
H7 H 0.493479 1.198084 0.291943 0.067 Uiso 1 1 calc R . . . .
C8 C 0.0706(2) 1.2223(4) 0.38998(15) 0.0832(6) Uani 1 1 d . . . . .
H8A H 0.000639 1.123008 0.358595 0.125 Uiso 1 1 calc GR . . . .
H8B H 0.067047 1.374281 0.360546 0.125 Uiso 1 1 calc GR . . . .
H8C H 0.055381 1.239081 0.454700 0.125 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.340(2) . ?
N1 C1 1.295(2) . ?
N2 N3 1.280(2) . ?
N3 N4 1.3389(19) . ?
N4 C1 1.3198(19) . ?
N4 C2 1.4245(19) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(2) . ?
C2 C7 1.368(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(2) . ?
C5 C6 1.380(2) . ?
C5 C8 1.499(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(2) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C1 N1 N2 105.06(15) . . ?
N3 N2 N1 110.91(14) . . ?
N2 N3 N4 106.89(14) . . ?
N3 N4 C2 121.94(13) . . ?
C1 N4 N3 106.75(14) . . ?
C1 N4 C2 131.30(14) . . ?
N1 C1 N4 110.38(16) . . ?
N1 C1 H1 124.8 . . ?
N4 C1 H1 124.8 . . ?
C3 C2 N4 119.62(15) . . ?
C7 C2 N4 119.41(14) . . ?
C7 C2 C3 120.96(15) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.82(16) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 121.97(15) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 117.59(16) . . ?
C4 C5 C8 121.57(16) . . ?
C6 C5 C8 120.84(17) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.55(16) . . ?
C7 C6 H6 119.2 . . ?
C2 C7 C6 119.08(15) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 N3 N4 0.5(2) . . . . ?
N2 N1 C1 N4 -0.9(2) . . . . ?
N2 N3 N4 C1 -1.02(19) . . . . ?
N2 N3 N4 C2 179.76(14) . . . . ?
N3 N4 C1 N1 1.21(19) . . . . ?
N3 N4 C2 C3 21.4(2) . . . . ?
N3 N4 C2 C7 -158.26(15) . . . . ?
N4 C2 C3 C4 179.96(13) . . . . ?
N4 C2 C7 C6 -178.87(13) . . . . ?
C1 N1 N2 N3 0.2(2) . . . . ?
C1 N4 C2 C3 -157.61(16) . . . . ?
C1 N4 C2 C7 22.7(2) . . . . ?
C2 N4 C1 N1 -179.67(15) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C2 C7 C6 1.5(2) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C3 C4 C5 C8 -178.98(16) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C2 -1.3(3) . . . . ?
C7 C2 C3 C4 -0.4(2) . . . . ?
C8 C5 C6 C7 -179.89(15) . . . . ?

_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.671
####################################################################### 
# 
# 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_exp_6812
_database_code_depnum_ccdc_archive 'CCDC 1917630'
loop_
_audit_author_name
_audit_author_address
'Ya Wang'
;Huaqiao University
China
;
_audit_update_record             
;
2019-05-22 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;
_audit_creation_date             2019-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 N2 O2'
_chemical_formula_sum            'C14 H16 N2 O2'
_chemical_formula_weight         244.29
_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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1279(14)
_cell_length_b                   8.6652(15)
_cell_length_c                   18.746(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.939(14)
_cell_angle_gamma                90
_cell_volume                     1310.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1072
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.0680
_cell_measurement_theta_min      3.9380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5213
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.450
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  81.00   1.00    3.00    --   15.49  77.00 -60.00   83
  2  ω    -63.00  43.00   1.00    3.00    --  -16.28   0.00 -60.00  106
  3  ω    -20.00  12.00   1.00    3.00    --  -16.28 -99.00 150.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0456220000
_diffrn_orient_matrix_UB_12      -0.0576033000
_diffrn_orient_matrix_UB_13      -0.0207379000
_diffrn_orient_matrix_UB_21      -0.0137369000
_diffrn_orient_matrix_UB_22      0.0520988000
_diffrn_orient_matrix_UB_23      -0.0293254000
_diffrn_orient_matrix_UB_31      0.0737795000
_diffrn_orient_matrix_UB_32      -0.0258758000
_diffrn_orient_matrix_UB_33      -0.0128416000
_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                1333
_reflns_number_total             2276
_reflns_odcompleteness_completeness 96.89
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0743
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1881
_refine_ls_wR_factor_ref         0.2180
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00H(H00J,H00K)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00B(H00B), C00D(H00D), C00E(H00E)
2.c Idealised Me refined as rotating group:
 C00F(H00A,H00C,H00F), C00G(H00G,H00H,H00I), C00I(H00L,H00M,H00N)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.4887(3) 0.3104(3) 0.30372(12) 0.0774(8) Uani 1 1 d . . . . .
N002 N 0.6857(3) 0.7695(3) 0.38328(11) 0.0538(7) Uani 1 1 d . . . . .
O003 O 0.4313(4) 0.3602(3) 0.41408(13) 0.0952(9) Uani 1 1 d . . . . .
N004 N 0.6500(4) 0.5926(3) 0.29724(13) 0.0759(9) Uani 1 1 d . . . . .
C005 C 0.7362(3) 0.9099(4) 0.42030(14) 0.0529(8) Uani 1 1 d . . . . .
C006 C 0.5789(4) 0.5437(4) 0.35580(14) 0.0565(8) Uani 1 1 d . . . . .
C007 C 0.6017(4) 0.6507(4) 0.40886(14) 0.0560(8) Uani 1 1 d . . . . .
H007 H 0.5664 0.6438 0.4541 0.067 Uiso 1 1 calc R . . . .
C008 C 0.8183(4) 1.0229(4) 0.38706(15) 0.0614(9) Uani 1 1 d . . . . .
H008 H 0.8420 1.0077 0.3403 0.074 Uiso 1 1 calc R . . . .
C009 C 0.4936(4) 0.3980(4) 0.36148(16) 0.0652(9) Uani 1 1 d . . . . .
C00A C 0.8663(4) 1.1596(4) 0.42264(17) 0.0631(9) Uani 1 1 d . . . . .
C00B C 0.7026(4) 0.9323(4) 0.48935(16) 0.0679(9) Uani 1 1 d . . . . .
H00B H 0.6476 0.8566 0.5125 0.081 Uiso 1 1 calc R . . . .
C00C C 0.8303(4) 1.1826(4) 0.49180(17) 0.0656(9) Uani 1 1 d . . . . .
C00D C 0.7116(5) 0.7274(4) 0.31550(16) 0.0761(11) Uani 1 1 d . . . . .
H00D H 0.7673 0.7886 0.2855 0.091 Uiso 1 1 calc R . . . .
C00E C 0.7508(4) 1.0677(4) 0.52425(17) 0.0763(11) Uani 1 1 d . . . . .
H00E H 0.7286 1.0815 0.5714 0.092 Uiso 1 1 calc R . . . .
C00F C 0.9579(5) 1.2798(5) 0.3845(2) 0.0874(12) Uani 1 1 d . . . . .
H00A H 0.9733 1.2431 0.3374 0.131 Uiso 1 1 calc GR . . . .
H00C H 1.0640 1.2990 0.4115 0.131 Uiso 1 1 calc GR . . . .
H00F H 0.8948 1.3736 0.3803 0.131 Uiso 1 1 calc GR . . . .
C00G C 0.8772(5) 1.3302(4) 0.5315(2) 0.0909(12) Uani 1 1 d . . . . .
H00G H 0.9950 1.3444 0.5350 0.136 Uiso 1 1 calc GR . . . .
H00H H 0.8439 1.3249 0.5789 0.136 Uiso 1 1 calc GR . . . .
H00I H 0.8226 1.4156 0.5060 0.136 Uiso 1 1 calc GR . . . .
C00H C 0.4060(6) 0.1617(5) 0.3084(2) 0.1034(14) Uani 1 1 d . . . . .
H00J H 0.4723 0.0970 0.3429 0.124 Uiso 1 1 calc R . . . .
H00K H 0.2995 0.1780 0.3256 0.124 Uiso 1 1 calc R . . . .
C00I C 0.3824(11) 0.0882(8) 0.2445(3) 0.195(4) Uani 1 1 d . . . . .
H00L H 0.3112 0.1491 0.2109 0.292 Uiso 1 1 calc GR . . . .
H00M H 0.3319 -0.0103 0.2505 0.292 Uiso 1 1 calc GR . . . .
H00N H 0.4872 0.0737 0.2267 0.292 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
O001 C009 1.319(4) . ?
O001 C00H 1.460(4) . ?
N002 C005 1.436(4) . ?
N002 C007 1.355(4) . ?
N002 C00D 1.362(4) . ?
O003 C009 1.207(4) . ?
N004 C006 1.368(4) . ?
N004 C00D 1.301(4) . ?
C005 C008 1.376(4) . ?
C005 C00B 1.369(4) . ?
C006 C007 1.356(4) . ?
C006 C009 1.451(5) . ?
C007 H007 0.9300 . ?
C008 H008 0.9300 . ?
C008 C00A 1.392(4) . ?
C00A C00C 1.378(4) . ?
C00A C00F 1.510(5) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.377(5) . ?
C00C C00E 1.369(5) . ?
C00C C00G 1.506(5) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00F H00A 0.9600 . ?
C00F H00C 0.9600 . ?
C00F H00F 0.9600 . ?
C00G H00G 0.9600 . ?
C00G H00H 0.9600 . ?
C00G H00I 0.9600 . ?
C00H H00J 0.9700 . ?
C00H H00K 0.9700 . ?
C00H C00I 1.349(6) . ?
C00I H00L 0.9600 . ?
C00I H00M 0.9600 . ?
C00I H00N 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
C009 O001 C00H 115.3(3) . . ?
C007 N002 C005 126.8(2) . . ?
C007 N002 C00D 105.5(3) . . ?
C00D N002 C005 127.6(3) . . ?
C00D N004 C006 104.7(2) . . ?
C008 C005 N002 120.7(3) . . ?
C00B C005 N002 120.0(3) . . ?
C00B C005 C008 119.4(3) . . ?
N004 C006 C009 125.4(3) . . ?
C007 C006 N004 110.1(3) . . ?
C007 C006 C009 124.4(3) . . ?
N002 C007 C006 106.8(2) . . ?
N002 C007 H007 126.6 . . ?
C006 C007 H007 126.6 . . ?
C005 C008 H008 119.6 . . ?
C005 C008 C00A 120.8(3) . . ?
C00A C008 H008 119.6 . . ?
O001 C009 C006 114.1(3) . . ?
O003 C009 O001 122.7(3) . . ?
O003 C009 C006 123.2(3) . . ?
C008 C00A C00F 119.1(3) . . ?
C00C C00A C008 119.7(3) . . ?
C00C C00A C00F 121.3(3) . . ?
C005 C00B H00B 120.2 . . ?
C005 C00B C00E 119.5(3) . . ?
C00E C00B H00B 120.2 . . ?
C00A C00C C00G 121.2(3) . . ?
C00E C00C C00A 118.6(3) . . ?
C00E C00C C00G 120.2(3) . . ?
N002 C00D H00D 123.6 . . ?
N004 C00D N002 112.8(3) . . ?
N004 C00D H00D 123.6 . . ?
C00B C00E H00E 119.0 . . ?
C00C C00E C00B 122.1(3) . . ?
C00C C00E H00E 119.0 . . ?
C00A C00F H00A 109.5 . . ?
C00A C00F H00C 109.5 . . ?
C00A C00F H00F 109.5 . . ?
H00A C00F H00C 109.5 . . ?
H00A C00F H00F 109.5 . . ?
H00C C00F H00F 109.5 . . ?
C00C C00G H00G 109.5 . . ?
C00C C00G H00H 109.5 . . ?
C00C C00G H00I 109.5 . . ?
H00G C00G H00H 109.5 . . ?
H00G C00G H00I 109.5 . . ?
H00H C00G H00I 109.5 . . ?
O001 C00H H00J 109.1 . . ?
O001 C00H H00K 109.1 . . ?
H00J C00H H00K 107.9 . . ?
C00I C00H O001 112.4(4) . . ?
C00I C00H H00J 109.1 . . ?
C00I C00H H00K 109.1 . . ?
C00H C00I H00L 109.5 . . ?
C00H C00I H00M 109.5 . . ?
C00H C00I H00N 109.5 . . ?
H00L C00I H00M 109.5 . . ?
H00L C00I H00N 109.5 . . ?
H00M C00I H00N 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_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 1.463
_oxdiff_exptl_absorpt_empirical_full_min 0.703
