# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_5-570
_database_code_depnum_ccdc_archive 'CCDC 1861984'
loop_
_audit_author_name
_audit_author_address
'Peijun Liu'
;Zunyi Medical Univeristy
China
;
_audit_update_record             
;
2018-08-14 deposited with the CCDC.	2019-03-06 downloaded from the CCDC.
;
_audit_creation_date             2018-07-10
_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         'C21 H17 N3 O2'
_chemical_formula_sum            'C21 H17 N3 O2'
_chemical_formula_weight         343.38
_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/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                   8.7751(5)
_cell_length_b                   13.7237(7)
_cell_length_c                   14.5990(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.524(6)
_cell_angle_gamma                90
_cell_volume                     1722.67(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3040
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.0170
_cell_measurement_theta_min      2.9080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (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    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9225
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.056
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  34.00   1.00    6.00    --   11.74 -57.00 -90.00   94
  2  ω    -15.00  76.00   1.00    6.00    --   11.74  77.00-180.00   91
  3  ω    -16.00  34.00   1.00    6.00    --   11.74  57.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0090724000
_diffrn_orient_matrix_UB_12      0.0509206000
_diffrn_orient_matrix_UB_13      0.0075915000
_diffrn_orient_matrix_UB_21      -0.0721133000
_diffrn_orient_matrix_UB_22      0.0015987000
_diffrn_orient_matrix_UB_23      0.0148497000
_diffrn_orient_matrix_UB_31      0.0389909000
_diffrn_orient_matrix_UB_32      -0.0088260000
_diffrn_orient_matrix_UB_33      0.0466889000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2404
_reflns_number_total             2973
_reflns_odcompleteness_completeness 97.04
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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         0.199
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.056
_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)+(0.0408P)²+0.4376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1070
_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:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C4(H4), C1(H1), C16(H16), C19(H19), C18(H18), C3(H3), C2(H2),
 C12(H12), C15(H15), C14(H14), C13(H13)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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
O1 O 0.55833(14) 0.31863(8) 0.44905(9) 0.0214(3) Uani 1 1 d . . . . .
O2 O 0.36319(14) 0.37158(9) 0.33587(10) 0.0294(4) Uani 1 1 d . . . . .
N1 N 0.76599(16) 0.15589(10) 0.48913(11) 0.0171(4) Uani 1 1 d . . . . .
N3 N 0.73330(16) 0.19971(10) 0.33188(11) 0.0203(4) Uani 1 1 d . . . . .
N2 N 0.97262(17) 0.23138(11) 0.43915(11) 0.0223(4) Uani 1 1 d . . . . .
C17 C 0.82671(19) 0.19804(12) 0.41602(13) 0.0176(4) Uani 1 1 d . . . . .
C8 C 0.60886(19) 0.15672(12) 0.49926(13) 0.0181(4) Uani 1 1 d . . . . .
C6 C 0.7437(2) 0.06160(12) 0.61331(13) 0.0184(4) Uani 1 1 d . . . . .
C7 C 0.5920(2) 0.10064(12) 0.57338(13) 0.0190(4) Uani 1 1 d . . . . .
C10 C 0.4858(2) 0.38619(13) 0.38921(13) 0.0201(4) Uani 1 1 d . . . . .
C20 C 0.7950(2) 0.23892(13) 0.26372(14) 0.0232(5) Uani 1 1 d . . . . .
H20 H 0.733643 0.243323 0.204069 0.028 Uiso 1 1 calc R . . . .
C5 C 0.8501(2) 0.09839(12) 0.56156(12) 0.0170(4) Uani 1 1 d . . . . .
C4 C 1.0084(2) 0.07593(12) 0.58463(13) 0.0197(4) Uani 1 1 d . . . . .
H4 H 1.077875 0.099634 0.549521 0.024 Uiso 1 1 calc R . . . .
C11 C 0.5753(2) 0.47912(13) 0.39554(13) 0.0203(4) Uani 1 1 d . . . . .
C1 C 0.7967(2) 0.00134(13) 0.69071(14) 0.0227(5) Uani 1 1 d . . . . .
H1 H 0.727701 -0.023965 0.725305 0.027 Uiso 1 1 calc R . . . .
C16 C 0.5087(2) 0.55938(13) 0.34411(13) 0.0212(4) Uani 1 1 d . . . . .
H16 H 0.408228 0.555069 0.308807 0.025 Uiso 1 1 calc R . . . .
C9 C 0.4916(2) 0.22095(12) 0.44019(14) 0.0211(4) Uani 1 1 d . . . . .
H9A H 0.472403 0.199724 0.375523 0.025 Uiso 1 1 calc R . . . .
H9B H 0.394238 0.219727 0.461995 0.025 Uiso 1 1 calc R . . . .
C19 C 0.9462(2) 0.27319(13) 0.27803(14) 0.0245(5) Uani 1 1 d . . . . .
H19 H 0.988327 0.298785 0.229588 0.029 Uiso 1 1 calc R . . . .
C18 C 1.0304(2) 0.26726(13) 0.36788(14) 0.0242(5) Uani 1 1 d . . . . .
H18 H 1.132646 0.289282 0.379818 0.029 Uiso 1 1 calc R . . . .
C3 C 1.0579(2) 0.01695(13) 0.66188(14) 0.0227(5) Uani 1 1 d . . . . .
H3 H 1.162817 0.001296 0.679192 0.027 Uiso 1 1 calc R . . . .
C2 C 0.9537(2) -0.01963(13) 0.71447(14) 0.0243(5) Uani 1 1 d . . . . .
H2 H 0.990598 -0.058667 0.766211 0.029 Uiso 1 1 calc R . . . .
C21 C 0.4476(2) 0.08231(13) 0.61075(14) 0.0245(5) Uani 1 1 d . . . . .
H21A H 0.461380 0.107018 0.673389 0.037 Uiso 1 1 calc GR . . . .
H21B H 0.427757 0.013533 0.610906 0.037 Uiso 1 1 calc GR . . . .
H21C H 0.361205 0.114644 0.571925 0.037 Uiso 1 1 calc GR . . . .
C12 C 0.7263(2) 0.48619(13) 0.44842(14) 0.0248(5) Uani 1 1 d . . . . .
H12 H 0.771715 0.433124 0.483107 0.030 Uiso 1 1 calc R . . . .
C15 C 0.5913(2) 0.64540(13) 0.34532(14) 0.0239(5) Uani 1 1 d . . . . .
H15 H 0.546209 0.698742 0.310938 0.029 Uiso 1 1 calc R . . . .
C14 C 0.7413(2) 0.65212(13) 0.39786(14) 0.0260(5) Uani 1 1 d . . . . .
H14 H 0.796838 0.709950 0.398688 0.031 Uiso 1 1 calc R . . . .
C13 C 0.8082(2) 0.57275(13) 0.44893(15) 0.0281(5) Uani 1 1 d . . . . .
H13 H 0.908849 0.577427 0.483915 0.034 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
O1 C10 1.344(2) . ?
O1 C9 1.458(2) . ?
O2 C10 1.212(2) . ?
N1 C17 1.409(2) . ?
N1 C8 1.416(2) . ?
N1 C5 1.405(2) . ?
N3 C17 1.334(2) . ?
N3 C20 1.337(2) . ?
N2 C17 1.338(2) . ?
N2 C18 1.339(2) . ?
C8 C7 1.360(3) . ?
C8 C9 1.491(2) . ?
C6 C7 1.445(2) . ?
C6 C5 1.407(3) . ?
C6 C1 1.402(3) . ?
C7 C21 1.497(3) . ?
C10 C11 1.491(3) . ?
C20 C19 1.383(3) . ?
C5 C4 1.397(2) . ?
C4 C3 1.386(3) . ?
C11 C16 1.394(2) . ?
C11 C12 1.397(2) . ?
C1 C2 1.381(3) . ?
C16 C15 1.383(3) . ?
C19 C18 1.373(3) . ?
C3 C2 1.399(3) . ?
C12 C13 1.388(3) . ?
C15 C14 1.388(3) . ?
C14 C13 1.383(3) . ?

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
C10 O1 C9 116.57(13) . . ?
C17 N1 C8 126.83(14) . . ?
C5 N1 C17 125.40(14) . . ?
C5 N1 C8 107.59(15) . . ?
C17 N3 C20 115.24(15) . . ?
C17 N2 C18 114.91(16) . . ?
N3 C17 N1 116.67(15) . . ?
N3 C17 N2 127.42(18) . . ?
N2 C17 N1 115.91(15) . . ?
N1 C8 C9 121.19(16) . . ?
C7 C8 N1 109.97(15) . . ?
C7 C8 C9 128.51(17) . . ?
C5 C6 C7 107.88(16) . . ?
C1 C6 C7 132.38(18) . . ?
C1 C6 C5 119.69(16) . . ?
C8 C7 C6 107.04(16) . . ?
C8 C7 C21 128.28(16) . . ?
C6 C7 C21 124.67(17) . . ?
O1 C10 C11 112.02(14) . . ?
O2 C10 O1 123.21(16) . . ?
O2 C10 C11 124.77(16) . . ?
N3 C20 C19 122.90(17) . . ?
N1 C5 C6 107.47(15) . . ?
C4 C5 N1 130.78(17) . . ?
C4 C5 C6 121.74(16) . . ?
C3 C4 C5 117.38(18) . . ?
C16 C11 C10 118.92(15) . . ?
C16 C11 C12 119.48(17) . . ?
C12 C11 C10 121.55(16) . . ?
C2 C1 C6 118.60(19) . . ?
C15 C16 C11 120.35(16) . . ?
O1 C9 C8 105.89(13) . . ?
C18 C19 C20 116.15(19) . . ?
N2 C18 C19 123.32(17) . . ?
C4 C3 C2 121.55(17) . . ?
C1 C2 C3 121.03(18) . . ?
C13 C12 C11 119.69(17) . . ?
C16 C15 C14 120.02(17) . . ?
C13 C14 C15 119.94(18) . . ?
C14 C13 C12 120.53(17) . . ?

_olex2_date_sample_data_collection 2018-07-10
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.762
####################################################################### 
# 
# 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_938
_database_code_depnum_ccdc_archive 'CCDC 1861986'
loop_
_audit_author_name
_audit_author_address
'Peijun Liu'
;Zunyi Medical Univeristy
China
;
_audit_update_record             
;
2018-08-14 deposited with the CCDC.	2019-03-06 downloaded from the CCDC.
;
_audit_creation_date             2018-05-31
_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         'C20 H15 N3 O2'
_chemical_formula_sum            'C20 H15 N3 O2'
_chemical_formula_weight         329.35
_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/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                   8.8758(8)
_cell_length_b                   14.7297(12)
_cell_length_c                   11.9629(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.831(9)
_cell_angle_gamma                90
_cell_volume                     1530.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3096
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.2390
_cell_measurement_theta_min      2.7080
_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  0.91566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (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    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8002
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.468
_diffrn_reflns_theta_min         2.222
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  29.00   1.00    3.00    --  -11.59 -99.00  30.00   42
  2  ω     -6.00  85.00   1.00    3.00    --   11.74  37.00-120.00   91
  3  ω    -20.00  44.00   1.00    3.00    --   11.74 -99.00 120.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0112339000
_diffrn_orient_matrix_UB_12      0.0338739000
_diffrn_orient_matrix_UB_13      -0.0429474000
_diffrn_orient_matrix_UB_21      0.0037180000
_diffrn_orient_matrix_UB_22      -0.0335935000
_diffrn_orient_matrix_UB_23      -0.0417741000
_diffrn_orient_matrix_UB_31      -0.0809295000
_diffrn_orient_matrix_UB_32      -0.0062710000
_diffrn_orient_matrix_UB_33      -0.0083764000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2910
_reflns_number_total             3637
_reflns_odcompleteness_completeness 99.94
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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         0.245
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3637
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.029
_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)+(0.0437P)²+0.5104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1144
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C20(H20), C16(H16), C12(H12), C4(H4), C18(H18), C5(H5),
 C19(H19), C3(H3), C13(H13), C14(H14), C15(H15)
;
_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
O1 O 0.37434(11) 0.57044(7) 0.42747(8) 0.0170(2) Uani 1 1 d . . . . .
O2 O 0.32809(12) 0.55731(8) 0.23615(9) 0.0216(3) Uani 1 1 d . . . . .
N1 N 0.14119(13) 0.43922(8) 0.59428(10) 0.0145(3) Uani 1 1 d . . . . .
N3 N 0.06235(14) 0.36033(9) 0.42449(10) 0.0181(3) Uani 1 1 d . . . . .
N2 N -0.04300(14) 0.32527(9) 0.58764(11) 0.0188(3) Uani 1 1 d . . . . .
C17 C 0.04895(15) 0.37141(10) 0.53244(12) 0.0151(3) Uani 1 1 d . . . . .
C11 C 0.50219(16) 0.67138(10) 0.32790(12) 0.0166(3) Uani 1 1 d . . . . .
C8 C 0.24885(16) 0.49472(10) 0.55322(12) 0.0151(3) Uani 1 1 d . . . . .
C1 C 0.15450(16) 0.45881(10) 0.71142(12) 0.0150(3) Uani 1 1 d . . . . .
C7 C 0.32664(16) 0.54519(10) 0.64017(12) 0.0165(3) Uani 1 1 d . . . . .
H7 H 0.403627 0.586937 0.635290 0.020 Uiso 1 1 calc R . . . .
C10 C 0.39280(16) 0.59394(10) 0.32276(12) 0.0161(3) Uani 1 1 d . . . . .
C9 C 0.26903(16) 0.49603(10) 0.43227(12) 0.0158(3) Uani 1 1 d . . . . .
H9A H 0.312012 0.439110 0.412587 0.019 Uiso 1 1 calc R . . . .
H9B H 0.171366 0.506323 0.380207 0.019 Uiso 1 1 calc R . . . .
C2 C 0.07377(17) 0.42633(10) 0.79161(13) 0.0176(3) Uani 1 1 d . . . . .
H2 H -0.005808 0.384604 0.771493 0.021 Uiso 1 1 calc R . . . .
C6 C 0.27133(16) 0.52395(10) 0.74085(13) 0.0168(3) Uani 1 1 d . . . . .
C20 C -0.02805(17) 0.29670(11) 0.36635(13) 0.0208(3) Uani 1 1 d . . . . .
H20 H -0.023423 0.286939 0.290324 0.025 Uiso 1 1 calc R . . . .
C16 C 0.54882(16) 0.72237(10) 0.42662(13) 0.0187(3) Uani 1 1 d . . . . .
H16 H 0.511162 0.708609 0.491659 0.022 Uiso 1 1 calc R . . . .
C12 C 0.55994(17) 0.69237(11) 0.23095(13) 0.0192(3) Uani 1 1 d . . . . .
H12 H 0.529369 0.658688 0.164408 0.023 Uiso 1 1 calc R . . . .
C4 C 0.23589(18) 0.52112(11) 0.93380(13) 0.0224(4) Uani 1 1 d . . . . .
H4 H 0.263295 0.540420 1.009259 0.027 Uiso 1 1 calc R . . . .
C18 C -0.13016(17) 0.26164(11) 0.52635(13) 0.0205(3) Uani 1 1 d . . . . .
H18 H -0.195141 0.227304 0.561517 0.025 Uiso 1 1 calc R . . . .
C5 C 0.31352(18) 0.55454(11) 0.85353(13) 0.0206(3) Uani 1 1 d . . . . .
H5 H 0.392423 0.596640 0.874138 0.025 Uiso 1 1 calc R . . . .
C19 C -0.12836(17) 0.24452(11) 0.41375(14) 0.0220(3) Uani 1 1 d . . . . .
H19 H -0.190846 0.200480 0.371923 0.026 Uiso 1 1 calc R . . . .
C3 C 0.11655(18) 0.45854(11) 0.90226(13) 0.0206(3) Uani 1 1 d . . . . .
H3 H 0.064296 0.437904 0.957220 0.025 Uiso 1 1 calc R . . . .
C13 C 0.66302(17) 0.76357(11) 0.23397(13) 0.0216(3) Uani 1 1 d . . . . .
H13 H 0.702310 0.776975 0.169544 0.026 Uiso 1 1 calc R . . . .
C14 C 0.70770(17) 0.81466(11) 0.33192(14) 0.0221(4) Uani 1 1 d . . . . .
H14 H 0.775440 0.862979 0.333071 0.027 Uiso 1 1 calc R . . . .
C15 C 0.65113(17) 0.79361(11) 0.42860(14) 0.0215(3) Uani 1 1 d . . . . .
H15 H 0.682019 0.827451 0.494976 0.026 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
O1 C10 1.3416(17) . ?
O1 C9 1.4492(17) . ?
O2 C10 1.2044(17) . ?
N1 C17 1.4024(18) . ?
N1 C8 1.4195(19) . ?
N1 C1 1.4118(18) . ?
N3 C17 1.3309(19) . ?
N3 C20 1.3331(19) . ?
N2 C17 1.3361(19) . ?
N2 C18 1.3349(19) . ?
C11 C10 1.491(2) . ?
C11 C16 1.389(2) . ?
C11 C12 1.395(2) . ?
C8 C7 1.348(2) . ?
C8 C9 1.494(2) . ?
C1 C2 1.394(2) . ?
C1 C6 1.404(2) . ?
C7 C6 1.425(2) . ?
C2 C3 1.384(2) . ?
C6 C5 1.398(2) . ?
C20 C19 1.383(2) . ?
C16 C15 1.385(2) . ?
C12 C13 1.387(2) . ?
C4 C5 1.382(2) . ?
C4 C3 1.396(2) . ?
C18 C19 1.374(2) . ?
C13 C14 1.381(2) . ?
C14 C15 1.387(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
C10 O1 C9 115.81(11) . . ?
C17 N1 C8 126.10(12) . . ?
C17 N1 C1 126.17(12) . . ?
C1 N1 C8 107.49(11) . . ?
C17 N3 C20 115.37(13) . . ?
C18 N2 C17 115.44(13) . . ?
N3 C17 N1 116.13(13) . . ?
N3 C17 N2 127.04(13) . . ?
N2 C17 N1 116.83(13) . . ?
C16 C11 C10 121.78(14) . . ?
C16 C11 C12 119.38(14) . . ?
C12 C11 C10 118.84(13) . . ?
N1 C8 C9 124.43(12) . . ?
C7 C8 N1 108.98(13) . . ?
C7 C8 C9 126.59(13) . . ?
C2 C1 N1 131.49(14) . . ?
C2 C1 C6 121.29(14) . . ?
C6 C1 N1 107.21(13) . . ?
C8 C7 C6 108.69(13) . . ?
O1 C10 C11 111.23(12) . . ?
O2 C10 O1 124.03(14) . . ?
O2 C10 C11 124.74(14) . . ?
O1 C9 C8 104.75(11) . . ?
C3 C2 C1 117.48(14) . . ?
C1 C6 C7 107.62(13) . . ?
C5 C6 C1 120.03(14) . . ?
C5 C6 C7 132.34(15) . . ?
N3 C20 C19 123.10(15) . . ?
C15 C16 C11 120.29(15) . . ?
C13 C12 C11 119.90(15) . . ?
C5 C4 C3 120.40(14) . . ?
N2 C18 C19 123.07(14) . . ?
C4 C5 C6 118.82(15) . . ?
C18 C19 C20 115.97(14) . . ?
C2 C3 C4 121.93(15) . . ?
C14 C13 C12 120.49(15) . . ?
C13 C14 C15 119.72(15) . . ?
C16 C15 C14 120.22(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.251
_oxdiff_exptl_absorpt_empirical_full_min 0.712
