# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_n191217a
_database_code_depnum_ccdc_archive 'CCDC 2033676'
_audit_update_record             
;
2020-09-24 deposited with the CCDC.	2021-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 Br N2 O'
_chemical_formula_weight         367.24

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   10.730(4)
_cell_length_b                   9.218(3)
_cell_length_c                   16.091(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.635(7)
_cell_angle_gamma                90
_cell_volume                     1583.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1719
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      23.90

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            GREEN
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   0.598
_exptl_transmission_factor_max   0.652
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.601
_shelx_estimated_absorpt_T_min   0.598
_shelx_estimated_absorpt_T_max   0.652
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10044
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.907
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3285
_reflns_number_gt                2215
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0312P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3285
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.62980(3) 0.52825(4) 0.21186(2) 0.04612(14) Uani 1 1 d . . . . .
N1 N 0.4741(2) 0.5400(3) 0.33640(15) 0.0348(6) Uani 1 1 d . . . . .
N2 N 0.2626(2) 0.5526(3) 0.49474(17) 0.0437(7) Uani 1 1 d . . . . .
O1 O 0.2653(2) 0.8942(3) 0.44597(15) 0.0606(7) Uani 1 1 d . . . . .
C1 C 0.5677(3) 0.6092(3) 0.30813(18) 0.0340(7) Uani 1 1 d . . . . .
C2 C 0.6232(3) 0.7317(3) 0.3439(2) 0.0422(8) Uani 1 1 d . . . . .
H2 H 0.6892 0.7779 0.3213 0.051 Uiso 1 1 calc R U . . .
C3 C 0.5760(3) 0.7817(3) 0.4142(2) 0.0396(8) Uani 1 1 d . . . . .
H3 H 0.6118 0.8634 0.4407 0.048 Uiso 1 1 calc R U . . .
C4 C 0.4760(3) 0.7143(3) 0.44768(19) 0.0333(7) Uani 1 1 d . . . . .
C5 C 0.4264(2) 0.5921(3) 0.40541(18) 0.0315(7) Uani 1 1 d . . . . .
C6 C 0.3205(3) 0.5041(3) 0.4313(2) 0.0327(7) Uani 1 1 d . . . . .
C7 C 0.2850(3) 0.3766(3) 0.3900(2) 0.0431(8) Uani 1 1 d . . . . .
H7 H 0.3258 0.3460 0.3447 0.052 Uiso 1 1 calc R U . . .
C8 C 0.1884(3) 0.2956(4) 0.4168(2) 0.0528(9) Uani 1 1 d . . . . .
H8 H 0.1642 0.2086 0.3907 0.063 Uiso 1 1 calc R U . . .
C9 C 0.1291(3) 0.3460(4) 0.4822(2) 0.0529(9) Uani 1 1 d . . . . .
H9 H 0.0628 0.2948 0.5011 0.064 Uiso 1 1 calc R U . . .
C10 C 0.1692(3) 0.4731(4) 0.5193(2) 0.0532(9) Uani 1 1 d . . . . .
H10 H 0.1289 0.5061 0.5643 0.064 Uiso 1 1 calc R U . . .
C11 C 0.4314(3) 0.7745(3) 0.52535(19) 0.0378(8) Uani 1 1 d . . . . .
H11A H 0.4920 0.8451 0.5489 0.045 Uiso 1 1 calc R U . . .
H11B H 0.4283 0.6965 0.5656 0.045 Uiso 1 1 calc R U . . .
C12 C 0.3043(3) 0.8460(3) 0.5135(2) 0.0353(7) Uani 1 1 d . . . . .
C13 C 0.2327(3) 0.8660(3) 0.58698(19) 0.0344(7) Uani 1 1 d . . . . .
C14 C 0.1302(3) 0.9578(3) 0.5797(2) 0.0425(8) Uani 1 1 d . . . . .
H14 H 0.1099 1.0076 0.5299 0.051 Uiso 1 1 calc R U . . .
C15 C 0.0582(3) 0.9766(4) 0.6446(2) 0.0494(9) Uani 1 1 d . . . . .
H15 H -0.0103 1.0388 0.6379 0.059 Uiso 1 1 calc R U . . .
C16 C 0.0849(3) 0.9054(4) 0.7196(2) 0.0467(9) Uani 1 1 d . . . . .
C17 C 0.1889(3) 0.8176(4) 0.7269(2) 0.0533(9) Uani 1 1 d . . . . .
H17 H 0.2104 0.7700 0.7772 0.064 Uiso 1 1 calc R U . . .
C18 C 0.2620(3) 0.7979(4) 0.6626(2) 0.0478(9) Uani 1 1 d . . . . .
H18 H 0.3320 0.7380 0.6701 0.057 Uiso 1 1 calc R U . . .
C19 C 0.0040(3) 0.9216(5) 0.7891(2) 0.0733(12) Uani 1 1 d . . . . .
H19A H -0.0316 1.0172 0.7875 0.110 Uiso 1 1 d R U . . .
H19B H 0.0533 0.9073 0.8415 0.110 Uiso 1 1 d R U . . .
H19C H -0.0619 0.8509 0.7830 0.110 Uiso 1 1 d R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.899(3) . ?
N1 C1 1.309(4) . ?
N1 C5 1.355(4) . ?
N2 C6 1.324(4) . ?
N2 C10 1.333(4) . ?
O1 C12 1.210(3) . ?
C1 C2 1.376(4) . ?
C2 C3 1.365(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(4) . ?
C4 C11 1.489(4) . ?
C5 C6 1.489(4) . ?
C6 C7 1.385(4) . ?
C7 C8 1.381(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.364(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.509(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.483(4) . ?
C13 C18 1.378(4) . ?
C13 C14 1.384(4) . ?
C14 C15 1.369(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(5) . ?
C16 C19 1.489(5) . ?
C17 C18 1.370(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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 C5 118.4(3) . . ?
C6 N2 C10 117.8(3) . . ?
N1 C1 C2 124.8(3) . . ?
N1 C1 Br1 115.8(2) . . ?
C2 C1 Br1 119.4(2) . . ?
C3 C2 C1 116.3(3) . . ?
C3 C2 H2 121.8 . . ?
C1 C2 H2 121.8 . . ?
C2 C3 C4 122.2(3) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 116.3(3) . . ?
C5 C4 C11 124.9(3) . . ?
C3 C4 C11 118.8(3) . . ?
N1 C5 C4 122.0(3) . . ?
N1 C5 C6 113.3(2) . . ?
C4 C5 C6 124.7(3) . . ?
N2 C6 C7 121.9(3) . . ?
N2 C6 C5 117.4(3) . . ?
C7 C6 C5 120.6(3) . . ?
C8 C7 C6 119.3(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C9 C8 C7 118.5(3) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C10 118.6(3) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
N2 C10 C9 123.8(3) . . ?
N2 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
C4 C11 C12 114.7(2) . . ?
C4 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C4 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
O1 C12 C13 120.7(3) . . ?
O1 C12 C11 120.1(3) . . ?
C13 C12 C11 119.1(3) . . ?
C18 C13 C14 117.6(3) . . ?
C18 C13 C12 123.8(3) . . ?
C14 C13 C12 118.6(3) . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 121.5(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 116.9(3) . . ?
C17 C16 C19 121.6(3) . . ?
C15 C16 C19 121.5(3) . . ?
C18 C17 C16 122.3(3) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C17 C18 C13 120.5(3) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C16 C19 H19A 109.4 . . ?
C16 C19 H19B 109.6 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.6(4) . . . . ?
C5 N1 C1 Br1 179.5(2) . . . . ?
N1 C1 C2 C3 0.6(5) . . . . ?
Br1 C1 C2 C3 -178.2(2) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C2 C3 C4 C11 179.1(3) . . . . ?
C1 N1 C5 C4 -1.5(4) . . . . ?
C1 N1 C5 C6 180.0(2) . . . . ?
C3 C4 C5 N1 1.1(4) . . . . ?
C11 C4 C5 N1 -177.8(3) . . . . ?
C3 C4 C5 C6 179.4(3) . . . . ?
C11 C4 C5 C6 0.5(4) . . . . ?
C10 N2 C6 C7 1.2(5) . . . . ?
C10 N2 C6 C5 -178.8(3) . . . . ?
N1 C5 C6 N2 -175.5(3) . . . . ?
C4 C5 C6 N2 6.0(4) . . . . ?
N1 C5 C6 C7 4.6(4) . . . . ?
C4 C5 C6 C7 -173.9(3) . . . . ?
N2 C6 C7 C8 -1.5(5) . . . . ?
C5 C6 C7 C8 178.4(3) . . . . ?
C6 C7 C8 C9 1.4(5) . . . . ?
C7 C8 C9 C10 -1.1(5) . . . . ?
C6 N2 C10 C9 -0.8(5) . . . . ?
C8 C9 C10 N2 0.8(6) . . . . ?
C5 C4 C11 C12 -70.9(4) . . . . ?
C3 C4 C11 C12 110.3(3) . . . . ?
C4 C11 C12 O1 -24.4(4) . . . . ?
C4 C11 C12 C13 160.1(3) . . . . ?
O1 C12 C13 C18 170.7(3) . . . . ?
C11 C12 C13 C18 -13.8(4) . . . . ?
O1 C12 C13 C14 -9.1(4) . . . . ?
C11 C12 C13 C14 166.4(3) . . . . ?
C18 C13 C14 C15 -2.0(5) . . . . ?
C12 C13 C14 C15 177.8(3) . . . . ?
C13 C14 C15 C16 0.2(5) . . . . ?
C14 C15 C16 C17 1.6(5) . . . . ?
C14 C15 C16 C19 -177.8(3) . . . . ?
C15 C16 C17 C18 -1.5(5) . . . . ?
C19 C16 C17 C18 177.9(3) . . . . ?
C16 C17 C18 C13 -0.4(6) . . . . ?
C14 C13 C18 C17 2.1(5) . . . . ?
C12 C13 C18 C17 -177.7(3) . . . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_a200108a
_database_code_depnum_ccdc_archive 'CCDC 2034525'
_audit_update_record             
;
2020-09-29 deposited with the CCDC.	2021-04-20 downloaded from the CCDC.
;
_audit_creation_date             2020-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H11 Br N2 O'
_chemical_formula_sum            'C18 H11 Br N2 O'
_chemical_formula_weight         351.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.7732(5)
_cell_length_b                   7.7539(3)
_cell_length_c                   15.9751(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.728(4)
_cell_angle_gamma                90
_cell_volume                     1410.43(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2679
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4700
_cell_measurement_theta_min      3.8750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.992
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_av_unetI/netI     0.0876
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4725
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.045
_diffrn_reflns_theta_max         67.045
_diffrn_reflns_theta_min         3.882
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00 -10.00   1.00    1.24    --  -41.49 -77.00 -30.00   90
  2  ω    -20.00  11.00   1.00    1.24    --  -41.49 109.00 160.00   31
  3  ω     34.00  98.00   1.00    1.24    --   41.49-125.00-180.00   64
  4  ω     14.00  51.00   1.00    1.24    --   41.49  19.00 -30.00   37
  5  ω     74.00 118.00   1.00    4.98    --  107.08-125.00 120.00   44
  6  ω     33.00  61.00   1.00    4.98    --  107.08 -30.00 150.00   28
  7  ω     81.00 171.00   1.00    4.98    --  107.08  45.00 -30.00   90
  8  ω     35.00 110.00   1.00    4.98    --  107.08 -94.00 150.00   75
  9  ω     35.00  67.00   1.00    4.98    --  107.08-125.00 120.00   32
 10  ω     88.00 132.00   1.00    4.98    --  107.08 -30.00 150.00   44
 11  ω    125.00 157.00   1.00    4.98    --  107.08 125.00-150.00   32
 12  ω     88.00 163.00   1.00    4.98    --  107.08  45.00-120.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1262224000
_diffrn_orient_matrix_UB_12      0.0671997000
_diffrn_orient_matrix_UB_13      -0.0357462000
_diffrn_orient_matrix_UB_21      0.0000705000
_diffrn_orient_matrix_UB_22      0.0696331000
_diffrn_orient_matrix_UB_23      0.0903183000
_diffrn_orient_matrix_UB_31      0.0487658000
_diffrn_orient_matrix_UB_32      0.1735324000
_diffrn_orient_matrix_UB_33      -0.0224103000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2077
_reflns_number_total             2512
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         1.569
_refine_diff_density_min         -1.714
_refine_diff_density_rms         0.248
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2512
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0845
_refine_ls_restrained_S_all      1.045
_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)+(0.1680P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2077
_refine_ls_wR_factor_ref         0.2305
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.23338(4) 0.87553(7) 0.45671(4) 0.0258(3) Uani 1 1 d . . . . .
O1 O 0.9377(3) 0.6370(5) 0.5591(3) 0.0253(9) Uani 1 1 d . . . . .
N1 N 0.7156(4) 0.5626(6) 0.4390(3) 0.0189(9) Uani 1 1 d . . . . .
N2 N 0.4273(4) 0.7214(5) 0.4237(3) 0.0205(9) Uani 1 1 d . . . . .
C1 C 0.5998(5) 0.5851(7) 0.3908(3) 0.0203(11) Uani 1 1 d . . . . .
C2 C 0.5643(5) 0.5199(7) 0.3064(4) 0.0248(11) Uani 1 1 d . . . . .
H2 H 0.4872 0.5346 0.2741 0.030 Uiso 1 1 calc R . . . .
C3 C 0.6431(5) 0.4343(7) 0.2716(3) 0.0270(12) Uani 1 1 d . . . . .
H3 H 0.6204 0.3919 0.2153 0.032 Uiso 1 1 calc R . . . .
C4 C 0.7593(5) 0.4112(7) 0.3221(4) 0.0242(11) Uani 1 1 d . . . . .
H4 H 0.8129 0.3512 0.2992 0.029 Uiso 1 1 calc R . . . .
C5 C 0.7942(4) 0.4764(7) 0.4048(4) 0.0238(11) Uani 1 1 d . . . . .
H5 H 0.8712 0.4617 0.4372 0.029 Uiso 1 1 calc R . . . .
C6 C 0.7308(5) 0.6284(6) 0.5233(4) 0.0190(11) Uani 1 1 d . . . . .
C7 C 0.6210(4) 0.6945(7) 0.5269(4) 0.0211(11) Uani 1 1 d . . . . .
C8 C 0.5411(4) 0.6698(7) 0.4462(3) 0.0194(10) Uani 1 1 d . . . . .
C9 C 0.3933(4) 0.8006(6) 0.4853(3) 0.0202(10) Uani 1 1 d . . . . .
C10 C 0.4645(5) 0.8400(7) 0.5687(3) 0.0203(10) Uani 1 1 d . . . . .
H10 H 0.4343 0.9010 0.6083 0.024 Uiso 1 1 calc R . . . .
C11 C 0.5795(4) 0.7860(6) 0.5898(3) 0.0202(10) Uani 1 1 d . . . . .
H11 H 0.6288 0.8090 0.6441 0.024 Uiso 1 1 calc R . . . .
C12 C 0.8467(5) 0.6383(6) 0.5826(4) 0.0190(12) Uani 1 1 d . . . . .
C13 C 0.8531(5) 0.6499(7) 0.6769(4) 0.0201(11) Uani 1 1 d . . . . .
C14 C 0.7830(4) 0.5458(6) 0.7148(3) 0.0209(11) Uani 1 1 d . . . . .
H14 H 0.7250 0.4766 0.6805 0.025 Uiso 1 1 calc R . . . .
C15 C 0.8005(4) 0.5463(7) 0.8044(4) 0.0231(11) Uani 1 1 d . . . . .
H15 H 0.7542 0.4759 0.8295 0.028 Uiso 1 1 calc R . . . .
C16 C 0.8850(5) 0.6487(8) 0.8567(4) 0.0248(12) Uani 1 1 d . . . . .
H16 H 0.8963 0.6468 0.9165 0.030 Uiso 1 1 calc R . . . .
C17 C 0.9537(5) 0.7558(7) 0.8190(4) 0.0264(11) Uani 1 1 d . . . . .
H17 H 1.0093 0.8283 0.8535 0.032 Uiso 1 1 calc R . . . .
C18 C 0.9389(4) 0.7539(7) 0.7296(4) 0.0241(11) Uani 1 1 d . . . . .
H18 H 0.9866 0.8223 0.7049 0.029 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
Br1 C9 1.912(5) . ?
O1 C12 1.223(7) . ?
N1 C1 1.396(7) . ?
N1 C5 1.364(7) . ?
N1 C6 1.408(7) . ?
N2 C8 1.356(7) . ?
N2 C9 1.306(7) . ?
C1 C2 1.401(8) . ?
C1 C8 1.415(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.413(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.405(8) . ?
C6 C12 1.452(7) . ?
C7 C8 1.402(8) . ?
C7 C11 1.414(8) . ?
C9 C10 1.415(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.491(8) . ?
C13 C14 1.398(8) . ?
C13 C18 1.395(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.393(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.398(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.394(8) . ?
C18 H18 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
C1 N1 C6 110.5(4) . . ?
C5 N1 C1 120.5(5) . . ?
C5 N1 C6 128.8(5) . . ?
C9 N2 C8 114.2(4) . . ?
N1 C1 C2 119.7(5) . . ?
N1 C1 C8 106.1(4) . . ?
C2 C1 C8 134.1(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(5) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(5) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(5) . . ?
C5 C4 H4 119.6 . . ?
N1 C5 C4 119.9(5) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
N1 C6 C12 120.9(5) . . ?
C7 C6 N1 106.1(5) . . ?
C7 C6 C12 132.4(5) . . ?
C6 C7 C11 134.4(5) . . ?
C8 C7 C6 108.7(5) . . ?
C8 C7 C11 116.7(5) . . ?
N2 C8 C1 125.3(5) . . ?
N2 C8 C7 126.1(5) . . ?
C7 C8 C1 108.6(5) . . ?
N2 C9 Br1 115.8(4) . . ?
N2 C9 C10 126.1(5) . . ?
C10 C9 Br1 118.1(4) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.4(5) . . ?
C11 C10 H10 120.8 . . ?
C7 C11 H11 120.8 . . ?
C10 C11 C7 118.4(5) . . ?
C10 C11 H11 120.8 . . ?
O1 C12 C6 123.4(6) . . ?
O1 C12 C13 119.2(5) . . ?
C6 C12 C13 117.4(5) . . ?
C14 C13 C12 121.3(5) . . ?
C18 C13 C12 119.2(5) . . ?
C18 C13 C14 119.2(5) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(5) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.3(5) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.3(5) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.0(5) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.5(5) . . ?
C17 C18 H18 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C9 C10 C11 179.8(4) . . . . ?
O1 C12 C13 C14 -135.8(5) . . . . ?
O1 C12 C13 C18 37.6(7) . . . . ?
N1 C1 C2 C3 0.0(8) . . . . ?
N1 C1 C8 N2 177.6(5) . . . . ?
N1 C1 C8 C7 -1.0(6) . . . . ?
N1 C6 C7 C8 -0.3(6) . . . . ?
N1 C6 C7 C11 -175.3(5) . . . . ?
N1 C6 C12 O1 20.4(7) . . . . ?
N1 C6 C12 C13 -159.3(4) . . . . ?
N2 C9 C10 C11 -2.6(8) . . . . ?
C1 N1 C5 C4 0.0(8) . . . . ?
C1 N1 C6 C7 -0.3(5) . . . . ?
C1 N1 C6 C12 -172.8(4) . . . . ?
C1 C2 C3 C4 0.8(8) . . . . ?
C2 C1 C8 N2 -5.7(10) . . . . ?
C2 C1 C8 C7 175.8(6) . . . . ?
C2 C3 C4 C5 -1.3(9) . . . . ?
C3 C4 C5 N1 0.8(8) . . . . ?
C5 N1 C1 C2 -0.5(7) . . . . ?
C5 N1 C1 C8 176.8(5) . . . . ?
C5 N1 C6 C7 -175.9(5) . . . . ?
C5 N1 C6 C12 11.6(8) . . . . ?
C6 N1 C1 C2 -176.5(5) . . . . ?
C6 N1 C1 C8 0.8(6) . . . . ?
C6 N1 C5 C4 175.3(5) . . . . ?
C6 C7 C8 N2 -177.8(5) . . . . ?
C6 C7 C8 C1 0.8(6) . . . . ?
C6 C7 C11 C10 176.3(6) . . . . ?
C6 C12 C13 C14 43.9(7) . . . . ?
C6 C12 C13 C18 -142.7(5) . . . . ?
C7 C6 C12 O1 -149.7(6) . . . . ?
C7 C6 C12 C13 30.6(8) . . . . ?
C8 N2 C9 Br1 -179.9(3) . . . . ?
C8 N2 C9 C10 2.4(7) . . . . ?
C8 C1 C2 C3 -176.4(6) . . . . ?
C8 C7 C11 C10 1.6(7) . . . . ?
C9 N2 C8 C1 -178.5(5) . . . . ?
C9 N2 C8 C7 -0.2(7) . . . . ?
C9 C10 C11 C7 0.3(7) . . . . ?
C11 C7 C8 N2 -1.8(8) . . . . ?
C11 C7 C8 C1 176.8(4) . . . . ?
C12 C6 C7 C8 170.9(5) . . . . ?
C12 C6 C7 C11 -4.1(10) . . . . ?
C12 C13 C14 C15 172.9(5) . . . . ?
C12 C13 C18 C17 -174.4(5) . . . . ?
C13 C14 C15 C16 0.6(8) . . . . ?
C14 C13 C18 C17 -0.9(8) . . . . ?
C14 C15 C16 C17 0.7(8) . . . . ?
C15 C16 C17 C18 -2.1(8) . . . . ?
C16 C17 C18 C13 2.2(8) . . . . ?
C18 C13 C14 C15 -0.6(7) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2020-01-08
_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 7.362
_oxdiff_exptl_absorpt_empirical_full_min 0.411
####################################################################### 
# 
# 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_a200710a
_database_code_depnum_ccdc_archive 'CCDC 2034526'
_audit_update_record             
;
2020-09-29 deposited with the CCDC.	2021-04-20 downloaded from the CCDC.
;
_audit_creation_date             2020-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 N2 O2'
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   8.8361(10)
_cell_length_b                   8.2497(8)
_cell_length_c                   21.719(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.488(11)
_cell_angle_gamma                90
_cell_volume                     1573.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2175
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.7080
_cell_measurement_theta_min      2.6470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7217
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.320
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     12.00  38.00   1.00   15.44    --   11.16 -99.00-180.00   26
  2  ω     -2.00  66.00   1.00   15.44    --   11.16  38.00-120.00   68
  3  ω    -20.00  87.00   1.00   15.44    --   11.16  77.00 -60.00  107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0205553000
_diffrn_orient_matrix_UB_12      -0.0072462000
_diffrn_orient_matrix_UB_13      -0.0304785000
_diffrn_orient_matrix_UB_21      0.0761867000
_diffrn_orient_matrix_UB_22      -0.0170888000
_diffrn_orient_matrix_UB_23      0.0122301000
_diffrn_orient_matrix_UB_31      -0.0171537000
_diffrn_orient_matrix_UB_32      -0.0840751000
_diffrn_orient_matrix_UB_33      0.0001612000
_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                1939
_reflns_number_total             2776
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.136
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2776
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.042
_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)+(0.0850P)²+0.1040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1575
_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:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.97760(18) 0.32515(18) 0.38545(8) 0.0770(5) Uani 1 1 d . . . . .
O2 O 0.54454(18) 0.83295(16) 0.46765(7) 0.0697(4) Uani 1 1 d . . . . .
N1 N 0.6305(2) 0.2447(2) 0.33093(10) 0.0847(6) Uani 1 1 d . . . . .
N2 N 0.54854(18) 0.58840(18) 0.41670(7) 0.0533(4) Uani 1 1 d . . . . .
C1 C 0.9489(2) 0.0415(2) 0.37709(9) 0.0555(5) Uani 1 1 d . . . . .
C2 C 1.0431(3) 0.0321(3) 0.33097(12) 0.0799(7) Uani 1 1 d . . . . .
H2 H 1.0806 0.1269 0.3152 0.096 Uiso 1 1 calc R . . . .
C3 C 1.0829(3) -0.1159(3) 0.30771(14) 0.0960(9) Uani 1 1 d . . . . .
H3 H 1.1461 -0.1202 0.2763 0.115 Uiso 1 1 calc R . . . .
C4 C 1.0290(3) -0.2566(3) 0.33110(12) 0.0775(7) Uani 1 1 d . . . . .
H4 H 1.0571 -0.3566 0.3162 0.093 Uiso 1 1 calc R . . . .
C5 C 0.9346(3) -0.2487(3) 0.37613(12) 0.0722(6) Uani 1 1 d . . . . .
H5 H 0.8971 -0.3438 0.3918 0.087 Uiso 1 1 calc R . . . .
C6 C 0.8939(3) -0.1015(2) 0.39884(10) 0.0652(6) Uani 1 1 d . . . . .
H6 H 0.8282 -0.0982 0.4294 0.078 Uiso 1 1 calc R . . . .
C7 C 0.9115(2) 0.2056(2) 0.40131(9) 0.0573(5) Uani 1 1 d . . . . .
C8 C 0.7995(2) 0.2170(2) 0.44844(10) 0.0645(6) Uani 1 1 d . . . . .
H8A H 0.7185 0.1391 0.4378 0.077 Uiso 1 1 calc R . . . .
H8B H 0.8508 0.1868 0.4887 0.077 Uiso 1 1 calc R . . . .
C9 C 0.7299(2) 0.3823(2) 0.45342(9) 0.0553(5) Uani 1 1 d . . . . .
C10 C 0.6112(2) 0.4394(2) 0.41163(8) 0.0504(5) Uani 1 1 d . . . . .
C11 C 0.6031(2) 0.6823(2) 0.46277(9) 0.0557(5) Uani 1 1 d . . . . .
C12 C 0.7203(2) 0.6370(3) 0.50709(9) 0.0612(6) Uani 1 1 d . . . . .
H12 H 0.7552 0.7064 0.5394 0.073 Uiso 1 1 calc R . . . .
C13 C 0.7833(2) 0.4868(3) 0.50183(9) 0.0615(6) Uani 1 1 d . . . . .
H13 H 0.8627 0.4537 0.5309 0.074 Uiso 1 1 calc R . . . .
C14 C 0.5413(2) 0.3467(2) 0.35728(9) 0.0546(5) Uani 1 1 d . . . . .
C15 C 0.5719(4) 0.1700(4) 0.27916(16) 0.1125(11) Uani 1 1 d . . . . .
H15 H 0.6347 0.1009 0.2597 0.135 Uiso 1 1 calc R . . . .
C16 C 0.4247(4) 0.1892(4) 0.25322(14) 0.1023(10) Uani 1 1 d . . . . .
H16 H 0.3886 0.1336 0.2173 0.123 Uiso 1 1 calc R . . . .
C17 C 0.3322(3) 0.2911(3) 0.28091(11) 0.0778(7) Uani 1 1 d . . . . .
H17 H 0.2315 0.3063 0.2644 0.093 Uiso 1 1 calc R . . . .
C18 C 0.3909(3) 0.3716(2) 0.33423(10) 0.0615(6) Uani 1 1 d . . . . .
H18 H 0.3299 0.4415 0.3543 0.074 Uiso 1 1 calc R . . . .
C19 C 0.4282(3) 0.8815(3) 0.42012(12) 0.0801(7) Uani 1 1 d . . . . .
H19A H 0.4674 0.8780 0.3807 0.120 Uiso 1 1 calc GR . . . .
H19B H 0.3961 0.9899 0.4281 0.120 Uiso 1 1 calc GR . . . .
H19C H 0.3429 0.8091 0.4196 0.120 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
O1 C7 1.216(2) . ?
O2 C11 1.355(2) . ?
O2 C19 1.429(3) . ?
N1 C14 1.326(3) . ?
N1 C15 1.335(3) . ?
N2 C10 1.357(2) . ?
N2 C11 1.313(2) . ?
C1 C2 1.375(3) . ?
C1 C6 1.379(3) . ?
C1 C7 1.502(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.357(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.505(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.505(3) . ?
C9 C10 1.390(3) . ?
C9 C13 1.400(3) . ?
C10 C14 1.481(3) . ?
C11 C12 1.384(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.368(3) . ?
C13 H13 0.9300 . ?
C14 C18 1.382(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.359(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(3) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C11 O2 C19 116.76(16) . . ?
C14 N1 C15 117.6(2) . . ?
C11 N2 C10 118.57(18) . . ?
C2 C1 C6 117.8(2) . . ?
C2 C1 C7 118.74(18) . . ?
C6 C1 C7 123.41(18) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.1(2) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.1(2) . . ?
C5 C6 H6 119.5 . . ?
O1 C7 C1 120.03(18) . . ?
O1 C7 C8 121.04(19) . . ?
C1 C7 C8 118.80(17) . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 C7 114.26(16) . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C10 C9 C8 123.01(18) . . ?
C10 C9 C13 116.53(18) . . ?
C13 C9 C8 120.45(19) . . ?
N2 C10 C9 122.60(17) . . ?
N2 C10 C14 113.28(17) . . ?
C9 C10 C14 124.12(17) . . ?
O2 C11 C12 117.12(17) . . ?
N2 C11 O2 119.36(19) . . ?
N2 C11 C12 123.51(18) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 C11 117.78(18) . . ?
C13 C12 H12 121.1 . . ?
C9 C13 H13 119.5 . . ?
C12 C13 C9 121.0(2) . . ?
C12 C13 H13 119.5 . . ?
N1 C14 C10 117.20(18) . . ?
N1 C14 C18 122.16(19) . . ?
C18 C14 C10 120.59(18) . . ?
N1 C15 H15 118.2 . . ?
N1 C15 C16 123.6(3) . . ?
C16 C15 H15 118.2 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.8(2) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.7(2) . . ?
C18 C17 H17 120.6 . . ?
C14 C18 C17 119.1(2) . . ?
C14 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C8 C9 24.0(3) . . . . ?
O2 C11 C12 C13 -178.34(17) . . . . ?
N1 C14 C18 C17 -1.8(3) . . . . ?
N1 C15 C16 C17 0.7(5) . . . . ?
N2 C10 C14 N1 148.47(19) . . . . ?
N2 C10 C14 C18 -29.1(2) . . . . ?
N2 C11 C12 C13 0.8(3) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C1 C7 C8 C9 -160.15(18) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
C2 C1 C7 O1 -8.5(3) . . . . ?
C2 C1 C7 C8 175.6(2) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
C6 C1 C7 O1 171.3(2) . . . . ?
C6 C1 C7 C8 -4.6(3) . . . . ?
C7 C1 C2 C3 179.0(2) . . . . ?
C7 C1 C6 C5 -178.39(19) . . . . ?
C7 C8 C9 C10 79.4(2) . . . . ?
C7 C8 C9 C13 -101.0(2) . . . . ?
C8 C9 C10 N2 179.61(17) . . . . ?
C8 C9 C10 C14 -1.0(3) . . . . ?
C8 C9 C13 C12 -179.60(18) . . . . ?
C9 C10 C14 N1 -31.0(3) . . . . ?
C9 C10 C14 C18 151.44(19) . . . . ?
C10 N2 C11 O2 178.34(16) . . . . ?
C10 N2 C11 C12 -0.7(3) . . . . ?
C10 C9 C13 C12 0.1(3) . . . . ?
C10 C14 C18 C17 175.65(17) . . . . ?
C11 N2 C10 C9 0.4(3) . . . . ?
C11 N2 C10 C14 -179.07(16) . . . . ?
C11 C12 C13 C9 -0.4(3) . . . . ?
C13 C9 C10 N2 0.0(3) . . . . ?
C13 C9 C10 C14 179.34(17) . . . . ?
C14 N1 C15 C16 -2.0(5) . . . . ?
C15 N1 C14 C10 -175.0(2) . . . . ?
C15 N1 C14 C18 2.6(3) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C14 0.4(3) . . . . ?
C19 O2 C11 N2 -1.9(3) . . . . ?
C19 O2 C11 C12 177.26(19) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2020-07-10
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.433
_oxdiff_exptl_absorpt_empirical_full_min 0.773
