# Electronic Supplementary Material (ESI) for ChemComm.
# 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_gouxy_1106
_database_code_depnum_ccdc_archive 'CCDC 1892347'
loop_
_audit_author_name
_audit_author_address
'Xue-Ya Gou'
;Lanzhou University
China
;
_audit_update_record             
;
2019-01-21 deposited with the CCDC.	2019-04-10 downloaded from the CCDC.
;
_audit_creation_date             2018-11-08
_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        
5-bromo-N-(tert-butyl)-2-(pyridin-2-yl)aniline
_chemical_formula_moiety         'C15 H17 Br N2'
_chemical_formula_sum            'C15 H17 Br N2'
_chemical_formula_weight         305.21
_chemical_absolute_configuration ?
_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'
Br Br -0.2901 2.4595 '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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   36.666(4)
_cell_length_b                   16.9718(19)
_cell_length_c                   9.1422(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5689.1(10)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    914
_cell_measurement_temperature    294.37(10)
_cell_measurement_theta_max      21.8930
_cell_measurement_theta_min      4.2720
_shelx_estimated_absorpt_T_max   0.724
_shelx_estimated_absorpt_T_min   0.626
_exptl_absorpt_coefficient_mu    2.875
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2496
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3346
_diffrn_reflns_point_group_measured_fraction_full 0.718
_diffrn_reflns_point_group_measured_fraction_max 0.706
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         25.971
_diffrn_reflns_theta_min         3.755
_diffrn_ambient_temperature      294.37(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -61.00  -36.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -57.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00   75.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000   60.0000 120
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0021232000
_diffrn_orient_matrix_UB_12      0.0393043000
_diffrn_orient_matrix_UB_13      -0.0249729000
_diffrn_orient_matrix_UB_21      0.0146857000
_diffrn_orient_matrix_UB_22      0.0053967000
_diffrn_orient_matrix_UB_23      0.0494720000
_diffrn_orient_matrix_UB_31      0.0124087000
_diffrn_orient_matrix_UB_32      -0.0131540000
_diffrn_orient_matrix_UB_33      -0.0542998000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.329
_reflns_Friedel_fraction_full    0.398
_reflns_Friedel_fraction_max     0.374
_reflns_number_gt                1504
_reflns_number_total             1977
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.023(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1977
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.002
_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)+(0.0695P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1349
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C8(H8), C11(H11), C4(H4), C10(H10), C2(H2A), C1(H1), C3(H3)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_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
Br1 Br -0.37105(3) -0.61066(7) -1.63899(13) 0.0753(4) Uani 1 1 d . . . . .
N1 N -0.51258(18) -0.8829(4) -1.6564(8) 0.0531(17) Uani 1 1 d . . . . .
C15 C -0.3941(3) -0.8987(7) -1.3843(14) 0.086(3) Uani 1 1 d . . . . .
H15A H -0.394432 -0.946014 -1.441734 0.128 Uiso 1 1 calc GR . . . .
H15B H -0.382366 -0.908959 -1.292300 0.128 Uiso 1 1 calc GR . . . .
H15C H -0.380833 -0.858499 -1.435797 0.128 Uiso 1 1 calc GR . . . .
N2 N -0.45166(19) -0.8525(4) -1.4960(7) 0.0488(17) Uani 1 1 d . . . . .
H2 H -0.469911 -0.882203 -1.517060 0.059 Uiso 1 1 calc R . . . .
C5 C -0.4943(2) -0.8473(4) -1.7655(8) 0.0408(18) Uani 1 1 d . . . . .
C6 C -0.4650(2) -0.7903(4) -1.7265(7) 0.0374(17) Uani 1 1 d . . . . .
C7 C -0.44413(19) -0.7955(4) -1.5954(7) 0.0337(16) Uani 1 1 d . . . . .
C8 C -0.4155(2) -0.7420(5) -1.5776(9) 0.0452(19) Uani 1 1 d . . . . .
H8 H -0.400469 -0.746083 -1.495864 0.054 Uiso 1 1 calc R . . . .
C11 C -0.4576(2) -0.7290(5) -1.8229(8) 0.047(2) Uani 1 1 d . . . . .
H11 H -0.472192 -0.723497 -1.905541 0.057 Uiso 1 1 calc R . . . .
C4 C -0.5028(2) -0.8628(5) -1.9111(9) 0.054(2) Uani 1 1 d . . . . .
H4 H -0.489922 -0.837965 -1.985751 0.065 Uiso 1 1 calc R . . . .
C9 C -0.4091(2) -0.6840(5) -1.6776(9) 0.047(2) Uani 1 1 d . . . . .
C10 C -0.4296(2) -0.6757(5) -1.8011(9) 0.051(2) Uani 1 1 d . . . . .
H10 H -0.424923 -0.635729 -1.868143 0.061 Uiso 1 1 calc R . . . .
C12 C -0.4332(2) -0.8708(5) -1.3573(8) 0.046(2) Uani 1 1 d . . . . .
C2 C -0.5491(3) -0.9495(6) -1.8359(12) 0.068(3) Uani 1 1 d . . . . .
H2A H -0.568110 -0.983934 -1.857543 0.081 Uiso 1 1 calc R . . . .
C1 C -0.5398(3) -0.9331(6) -1.6941(12) 0.070(3) Uani 1 1 d . . . . .
H1 H -0.552848 -0.957690 -1.619705 0.084 Uiso 1 1 calc R . . . .
C3 C -0.5299(3) -0.9141(6) -1.9436(11) 0.065(3) Uani 1 1 d . . . . .
H3 H -0.535295 -0.925058 -2.040835 0.078 Uiso 1 1 calc R . . . .
C14 C -0.4341(3) -0.8023(6) -1.2512(9) 0.063(3) Uani 1 1 d . . . . .
H14A H -0.421037 -0.816083 -1.163845 0.095 Uiso 1 1 calc GR . . . .
H14B H -0.458950 -0.790190 -1.226883 0.095 Uiso 1 1 calc GR . . . .
H14C H -0.422896 -0.757065 -1.295544 0.095 Uiso 1 1 calc GR . . . .
C13 C -0.4547(3) -0.9389(6) -1.2905(10) 0.065(3) Uani 1 1 d . . . . .
H13A H -0.453925 -0.983468 -1.355214 0.098 Uiso 1 1 calc GR . . . .
H13B H -0.479624 -0.923056 -1.276454 0.098 Uiso 1 1 calc GR . . . .
H13C H -0.444237 -0.953086 -1.198010 0.098 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
Br1 C9 1.902(8) . ?
N1 C5 1.345(10) . ?
N1 C1 1.358(11) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 C12 1.530(13) . ?
N2 H2 0.8600 . ?
N2 C7 1.355(9) . ?
N2 C12 1.472(10) . ?
C5 C6 1.490(11) . ?
C5 C4 1.392(12) . ?
C6 C7 1.424(9) . ?
C6 C11 1.390(10) . ?
C7 C8 1.398(10) . ?
C8 H8 0.9300 . ?
C8 C9 1.364(10) . ?
C11 H11 0.9300 . ?
C11 C10 1.383(11) . ?
C4 H4 0.9300 . ?
C4 C3 1.354(13) . ?
C9 C10 1.364(12) . ?
C10 H10 0.9300 . ?
C12 C14 1.516(11) . ?
C12 C13 1.528(11) . ?
C2 H2A 0.9300 . ?
C2 C1 1.369(14) . ?
C2 C3 1.352(13) . ?
C1 H1 0.9300 . ?
C3 H3 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C5 N1 C1 117.4(8) . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
C7 N2 H2 115.3 . . ?
C7 N2 C12 129.4(6) . . ?
C12 N2 H2 115.3 . . ?
N1 C5 C6 118.3(6) . . ?
N1 C5 C4 120.9(7) . . ?
C4 C5 C6 120.8(8) . . ?
C7 C6 C5 123.3(7) . . ?
C11 C6 C5 118.3(6) . . ?
C11 C6 C7 118.4(7) . . ?
N2 C7 C6 120.0(7) . . ?
N2 C7 C8 122.5(6) . . ?
C8 C7 C6 117.5(7) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.3(7) . . ?
C9 C8 H8 119.4 . . ?
C6 C11 H11 118.6 . . ?
C10 C11 C6 122.8(7) . . ?
C10 C11 H11 118.6 . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.6(9) . . ?
C3 C4 H4 120.2 . . ?
C8 C9 Br1 118.3(6) . . ?
C8 C9 C10 122.3(7) . . ?
C10 C9 Br1 119.3(6) . . ?
C11 C10 H10 121.3 . . ?
C9 C10 C11 117.5(8) . . ?
C9 C10 H10 121.3 . . ?
N2 C12 C15 111.0(7) . . ?
N2 C12 C14 112.2(7) . . ?
N2 C12 C13 105.4(7) . . ?
C14 C12 C15 111.2(8) . . ?
C14 C12 C13 108.3(7) . . ?
C13 C12 C15 108.4(8) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 H2A 121.0 . . ?
C3 C2 C1 117.9(9) . . ?
N1 C1 C2 123.5(10) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.6(9) . . ?
C2 C3 H3 119.7 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
Br1 C9 C10 C11 -178.2(6) . . . . ?
N1 C5 C6 C7 29.0(11) . . . . ?
N1 C5 C6 C11 -151.0(7) . . . . ?
N1 C5 C4 C3 0.2(12) . . . . ?
N2 C7 C8 C9 -178.3(7) . . . . ?
C5 N1 C1 C2 0.6(14) . . . . ?
C5 C6 C7 N2 -2.9(11) . . . . ?
C5 C6 C7 C8 175.0(7) . . . . ?
C5 C6 C11 C10 -176.1(7) . . . . ?
C5 C4 C3 C2 1.1(13) . . . . ?
C6 C5 C4 C3 -179.1(8) . . . . ?
C6 C7 C8 C9 3.9(11) . . . . ?
C6 C11 C10 C9 -1.2(12) . . . . ?
C7 N2 C12 C15 -64.8(11) . . . . ?
C7 N2 C12 C14 60.3(11) . . . . ?
C7 N2 C12 C13 178.0(8) . . . . ?
C7 C6 C11 C10 3.9(11) . . . . ?
C7 C8 C9 Br1 176.8(6) . . . . ?
C7 C8 C9 C10 -1.2(13) . . . . ?
C8 C9 C10 C11 -0.2(13) . . . . ?
C11 C6 C7 N2 177.0(7) . . . . ?
C11 C6 C7 C8 -5.1(10) . . . . ?
C4 C5 C6 C7 -151.7(7) . . . . ?
C4 C5 C6 C11 28.4(11) . . . . ?
C12 N2 C7 C6 177.5(8) . . . . ?
C12 N2 C7 C8 -0.3(12) . . . . ?
C1 N1 C5 C6 178.4(7) . . . . ?
C1 N1 C5 C4 -1.0(11) . . . . ?
C1 C2 C3 C4 -1.4(15) . . . . ?
C3 C2 C1 N1 0.6(15) . . . . ?

_olex2_date_sample_data_collection 2018-11-07
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether/ethyl acetate'
####################################################################### 
# 
# 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_gouxy_0318
_database_code_depnum_ccdc_archive 'CCDC 1904937'
loop_
_audit_author_name
_audit_author_address
'xueya gou'
;lanzhou university
China
;
_audit_update_record             
;
2019-03-22 deposited with the CCDC.	2019-04-10 downloaded from the CCDC.
;
_audit_creation_date             2019-03-22
_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         'C16 H18 N2 O'
_chemical_formula_sum            'C16 H18 N2 O'
_chemical_formula_weight         254.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.2862(10)
_cell_length_b                   8.9940(5)
_cell_length_c                   18.4405(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.429(6)
_cell_angle_gamma                90
_cell_volume                     2700.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1386
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4940
_cell_measurement_theta_min      4.2290
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4948
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.380
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -8.00   20.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega    2.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
  3 omega  -19.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000  -30.0000 111
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0192736000
_diffrn_orient_matrix_UB_12      0.0042058000
_diffrn_orient_matrix_UB_13      -0.0348571000
_diffrn_orient_matrix_UB_21      -0.0377773000
_diffrn_orient_matrix_UB_22      -0.0219932000
_diffrn_orient_matrix_UB_23      0.0150287000
_diffrn_orient_matrix_UB_31      -0.0098840000
_diffrn_orient_matrix_UB_32      0.0756501000
_diffrn_orient_matrix_UB_33      0.0063002000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2108
_reflns_number_total             2657
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2657
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.054
_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)+(0.0506P)²+2.5997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1338
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C16(H16),
 C17(H17)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_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
N1 N 0.15230(10) -0.00237(17) 0.35935(9) 0.0327(4) Uani 1 1 d . . . . .
H1 H 0.116988 0.025341 0.326625 0.039 Uiso 1 1 calc R . . . .
N2 N 0.12254(10) 0.16040(17) 0.23603(8) 0.0300(4) Uani 1 1 d . . . . .
C3 C 0.27011(11) 0.0792(2) 0.43345(10) 0.0275(4) Uani 1 1 d . . . . .
H3 H 0.265337 -0.003228 0.463491 0.033 Uiso 1 1 calc R . . . .
C4 C 0.22120(11) 0.22941(19) 0.33210(9) 0.0243(4) Uani 1 1 d . . . . .
O5 O 0.39668(10) 0.04674(17) 0.54499(8) 0.0478(4) Uani 1 1 d . . . . .
C6 C 0.21410(11) 0.09753(19) 0.37532(10) 0.0251(4) Uani 1 1 d . . . . .
C7 C 0.33265(12) 0.1811(2) 0.44740(10) 0.0279(4) Uani 1 1 d . . . . .
C8 C 0.16128(11) 0.2700(2) 0.27314(10) 0.0255(4) Uani 1 1 d . . . . .
C9 C 0.14636(13) 0.4192(2) 0.25615(10) 0.0315(5) Uani 1 1 d . . . . .
H9 H 0.172100 0.493988 0.283085 0.038 Uiso 1 1 calc R . . . .
C10 C 0.34092(12) 0.3058(2) 0.40375(10) 0.0302(4) Uani 1 1 d . . . . .
H10 H 0.383136 0.373552 0.412671 0.036 Uiso 1 1 calc R . . . .
C11 C 0.28557(12) 0.3276(2) 0.34702(10) 0.0288(4) Uani 1 1 d . . . . .
H11 H 0.291387 0.410808 0.317640 0.035 Uiso 1 1 calc R . . . .
C12 C 0.39169(13) 0.1571(2) 0.50778(11) 0.0349(5) Uani 1 1 d . . . . .
H12 H 0.428494 0.233622 0.518299 0.042 Uiso 1 1 calc R . . . .
C13 C 0.10936(13) -0.1389(2) 0.46884(11) 0.0367(5) Uani 1 1 d . . . . .
H13A H 0.150857 -0.090999 0.498421 0.055 Uiso 1 1 calc GR . . . .
H13B H 0.099235 -0.236733 0.487402 0.055 Uiso 1 1 calc GR . . . .
H13C H 0.059619 -0.081695 0.469622 0.055 Uiso 1 1 calc GR . . . .
C14 C 0.05476(13) 0.3429(2) 0.16092(11) 0.0356(5) Uani 1 1 d . . . . .
H14 H 0.019007 0.364139 0.122182 0.043 Uiso 1 1 calc R . . . .
C15 C 0.13861(11) -0.15044(19) 0.39086(10) 0.0268(4) Uani 1 1 d . . . . .
C16 C 0.07076(13) 0.1987(2) 0.18169(11) 0.0352(5) Uani 1 1 d . . . . .
H16 H 0.043864 0.122954 0.156344 0.042 Uiso 1 1 calc R . . . .
C17 C 0.09367(13) 0.4549(2) 0.19964(11) 0.0362(5) Uani 1 1 d . . . . .
H17 H 0.084238 0.553948 0.187518 0.043 Uiso 1 1 calc R . . . .
C18 C 0.21399(12) -0.2508(2) 0.38662(11) 0.0330(5) Uani 1 1 d . . . . .
H18A H 0.230468 -0.258118 0.337125 0.049 Uiso 1 1 calc GR . . . .
H18B H 0.200795 -0.347966 0.404445 0.049 Uiso 1 1 calc GR . . . .
H18C H 0.258096 -0.209372 0.415624 0.049 Uiso 1 1 calc GR . . . .
C19 C 0.06995(13) -0.2189(2) 0.34347(11) 0.0355(5) Uani 1 1 d . . . . .
H19A H 0.021746 -0.157760 0.345553 0.053 Uiso 1 1 calc GR . . . .
H19B H 0.057618 -0.316732 0.360912 0.053 Uiso 1 1 calc GR . . . .
H19C H 0.087452 -0.225058 0.294234 0.053 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 H1 0.8600 . ?
N1 C6 1.376(2) . ?
N1 C15 1.472(2) . ?
N2 C8 1.348(2) . ?
N2 C16 1.338(2) . ?
C3 H3 0.9300 . ?
C3 C6 1.400(3) . ?
C3 C7 1.389(3) . ?
C4 C6 1.435(2) . ?
C4 C8 1.488(3) . ?
C4 C11 1.393(3) . ?
O5 C12 1.208(2) . ?
C7 C10 1.389(3) . ?
C7 C12 1.469(3) . ?
C8 C9 1.398(3) . ?
C9 H9 0.9300 . ?
C9 C17 1.371(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 C15 1.530(3) . ?
C14 H14 0.9300 . ?
C14 C16 1.375(3) . ?
C14 C17 1.380(3) . ?
C15 C18 1.527(3) . ?
C15 C19 1.531(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
C6 N1 H1 115.7 . . ?
C6 N1 C15 128.57(15) . . ?
C15 N1 H1 115.7 . . ?
C16 N2 C8 118.03(16) . . ?
C6 C3 H3 119.2 . . ?
C7 C3 H3 119.2 . . ?
C7 C3 C6 121.65(17) . . ?
C6 C4 C8 123.22(16) . . ?
C11 C4 C6 119.01(16) . . ?
C11 C4 C8 117.73(16) . . ?
N1 C6 C3 123.12(16) . . ?
N1 C6 C4 119.31(16) . . ?
C3 C6 C4 117.55(16) . . ?
C3 C7 C12 120.41(17) . . ?
C10 C7 C3 120.44(17) . . ?
C10 C7 C12 119.14(17) . . ?
N2 C8 C4 118.81(16) . . ?
N2 C8 C9 120.76(17) . . ?
C9 C8 C4 120.42(17) . . ?
C8 C9 H9 120.1 . . ?
C17 C9 C8 119.83(18) . . ?
C17 C9 H9 120.1 . . ?
C7 C10 H10 120.5 . . ?
C11 C10 C7 118.92(17) . . ?
C11 C10 H10 120.5 . . ?
C4 C11 H11 118.8 . . ?
C10 C11 C4 122.33(17) . . ?
C10 C11 H11 118.8 . . ?
O5 C12 C7 125.79(18) . . ?
O5 C12 H12 117.1 . . ?
C7 C12 H12 117.1 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C13 H13A 109.5 . . ?
C15 C13 H13B 109.5 . . ?
C15 C13 H13C 109.5 . . ?
C16 C14 H14 121.2 . . ?
C16 C14 C17 117.57(18) . . ?
C17 C14 H14 121.2 . . ?
N1 C15 C13 111.31(16) . . ?
N1 C15 C18 112.61(15) . . ?
N1 C15 C19 104.71(14) . . ?
C13 C15 C19 108.89(16) . . ?
C18 C15 C13 110.97(16) . . ?
C18 C15 C19 108.04(16) . . ?
N2 C16 C14 124.27(19) . . ?
N2 C16 H16 117.9 . . ?
C14 C16 H16 117.9 . . ?
C9 C17 C14 119.51(18) . . ?
C9 C17 H17 120.2 . . ?
C14 C17 H17 120.2 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 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
N2 C8 C9 C17 -2.0(3) . . . . ?
C3 C7 C10 C11 0.8(3) . . . . ?
C3 C7 C12 O5 7.1(3) . . . . ?
C4 C8 C9 C17 177.19(17) . . . . ?
C6 N1 C15 C13 71.7(2) . . . . ?
C6 N1 C15 C18 -53.7(3) . . . . ?
C6 N1 C15 C19 -170.81(19) . . . . ?
C6 C3 C7 C10 0.5(3) . . . . ?
C6 C3 C7 C12 -178.55(18) . . . . ?
C6 C4 C8 N2 -30.8(3) . . . . ?
C6 C4 C8 C9 149.95(18) . . . . ?
C6 C4 C11 C10 -2.7(3) . . . . ?
C7 C3 C6 N1 178.97(18) . . . . ?
C7 C3 C6 C4 -2.7(3) . . . . ?
C7 C10 C11 C4 0.4(3) . . . . ?
C8 N2 C16 C14 0.4(3) . . . . ?
C8 C4 C6 N1 4.3(3) . . . . ?
C8 C4 C6 C3 -174.15(16) . . . . ?
C8 C4 C11 C10 175.30(17) . . . . ?
C8 C9 C17 C14 1.1(3) . . . . ?
C10 C7 C12 O5 -172.0(2) . . . . ?
C11 C4 C6 N1 -177.85(17) . . . . ?
C11 C4 C6 C3 3.7(3) . . . . ?
C11 C4 C8 N2 151.28(17) . . . . ?
C11 C4 C8 C9 -28.0(3) . . . . ?
C12 C7 C10 C11 179.77(18) . . . . ?
C15 N1 C6 C3 -8.7(3) . . . . ?
C15 N1 C6 C4 172.97(18) . . . . ?
C16 N2 C8 C4 -177.96(17) . . . . ?
C16 N2 C8 C9 1.3(3) . . . . ?
C16 C14 C17 C9 0.4(3) . . . . ?
C17 C14 C16 N2 -1.2(3) . . . . ?

_olex2_date_sample_data_collection 2019-03-18
_olex2_submission_special_instructions 'No special instructions were received'
