# 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_exp_189-hks-934-1
_database_code_depnum_ccdc_archive 'CCDC 1853080'
loop_
_audit_author_name
_audit_author_address
'Krishnan Rangan'
;BITS Pilani
India
;
_audit_update_record             
;
2018-07-03 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;
_audit_creation_date             2017-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 Br N O'
_chemical_formula_sum            'C22 H16 Br N O'
_chemical_formula_weight         390.27
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.7437(4)
_cell_length_b                   9.0981(5)
_cell_length_c                   11.3532(6)
_cell_angle_alpha                89.931(4)
_cell_angle_beta                 69.876(5)
_cell_angle_gamma                83.515(4)
_cell_volume                     841.91(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3832
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      29.6280
_cell_measurement_theta_min      3.5170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.450
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (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_density_diffrn    1.539
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12080
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.907
_diffrn_reflns_theta_min         3.562
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  54.00   0.50   32.11    --    0.00  37.00  90.00  102
  2  ω     12.00  89.00   0.50   32.11    --    0.00  77.00 -30.00  154
  3  ω    -66.00  30.00   0.50   32.11    --    0.00 -77.00 -30.00  192
  4  ω    -15.00  86.00   0.50   32.11    --    0.00  77.00 -90.00  202
  5  ω    -42.00  22.00   0.50   32.11    --    0.00 -19.00  90.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0583071000
_diffrn_orient_matrix_UB_12      0.0558021000
_diffrn_orient_matrix_UB_13      -0.0086387000
_diffrn_orient_matrix_UB_21      -0.0555221000
_diffrn_orient_matrix_UB_22      -0.0117390000
_diffrn_orient_matrix_UB_23      0.0606816000
_diffrn_orient_matrix_UB_31      0.0330226000
_diffrn_orient_matrix_UB_32      0.0539896000
_diffrn_orient_matrix_UB_33      0.0260316000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3158
_reflns_number_total             4229
_reflns_odcompleteness_completeness 99.71
_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 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (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         0.913
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1055
_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:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C18(H18), C4(H4), C9(H9), C11(H11), C12(H12), C15(H15), C21(H21),
 C19(H19), C5(H5), C13(H13), C20(H20), C14(H14), C6(H6)
;
_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
Br1 Br 0.79890(4) 0.06101(4) 0.49146(3) 0.02835(11) Uani 1 1 d . . . . .
O1 O 0.2434(3) 0.4307(2) 0.50519(19) 0.0212(4) Uani 1 1 d . . . . .
N1 N 0.3625(3) 0.4171(2) 0.6593(2) 0.0161(4) Uani 1 1 d . . . . .
C17 C 0.4680(3) 0.1505(3) 0.6513(3) 0.0155(5) Uani 1 1 d . . . . .
C3 C 0.0719(4) 0.6590(3) 0.9166(3) 0.0208(6) Uani 1 1 d . . . . .
H3 H 0.100820 0.659914 0.988051 0.025 Uiso 1 1 calc R . . . .
C22 C 0.5945(3) 0.0337(3) 0.6142(3) 0.0193(5) Uani 1 1 d . . . . .
C16 C 0.4915(3) 0.3005(3) 0.5936(3) 0.0167(5) Uani 1 1 d . . . . .
H16A H 0.595778 0.328081 0.592869 0.020 Uiso 1 1 calc R . . . .
H16B H 0.496424 0.292370 0.507156 0.020 Uiso 1 1 calc R . . . .
C7 C 0.2438(3) 0.4692(3) 0.6081(3) 0.0168(5) Uani 1 1 d . . . . .
C2 C 0.1682(3) 0.5728(3) 0.8096(3) 0.0174(5) Uani 1 1 d . . . . .
C18 C 0.3200(3) 0.1229(3) 0.7406(3) 0.0174(5) Uani 1 1 d . . . . .
H18 H 0.233153 0.198530 0.765991 0.021 Uiso 1 1 calc R . . . .
C4 C -0.0687(4) 0.7435(3) 0.9125(3) 0.0228(6) Uani 1 1 d . . . . .
H4 H -0.135186 0.801385 0.982788 0.027 Uiso 1 1 calc R . . . .
C9 C 0.4013(3) 0.4459(3) 0.8666(3) 0.0179(5) Uani 1 1 d . . . . .
H9 H 0.350235 0.491916 0.945701 0.021 Uiso 1 1 calc R . . . .
C10 C 0.5587(3) 0.3507(3) 0.8480(3) 0.0171(5) Uani 1 1 d . . . . .
C11 C 0.5590(4) 0.2291(3) 0.9241(3) 0.0202(6) Uani 1 1 d . . . . .
H11 H 0.462700 0.212148 0.987722 0.024 Uiso 1 1 calc R . . . .
C1 C 0.1211(3) 0.5726(3) 0.7048(3) 0.0163(5) Uani 1 1 d . . . . .
C12 C 0.7017(4) 0.1339(3) 0.9053(3) 0.0227(6) Uani 1 1 d . . . . .
H12 H 0.699865 0.052372 0.955118 0.027 Uiso 1 1 calc R . . . .
C15 C 0.7065(4) 0.3784(3) 0.7582(3) 0.0211(6) Uani 1 1 d . . . . .
H15 H 0.709575 0.461311 0.709772 0.025 Uiso 1 1 calc R . . . .
C21 C 0.5752(4) -0.1059(3) 0.6644(3) 0.0250(6) Uani 1 1 d . . . . .
H21 H 0.661132 -0.182267 0.637710 0.030 Uiso 1 1 calc R . . . .
C19 C 0.2988(4) -0.0160(3) 0.7930(3) 0.0233(6) Uani 1 1 d . . . . .
H19 H 0.199357 -0.031936 0.853362 0.028 Uiso 1 1 calc R . . . .
C5 C -0.1129(4) 0.7434(3) 0.8045(3) 0.0227(6) Uani 1 1 d . . . . .
H5 H -0.206698 0.802538 0.804040 0.027 Uiso 1 1 calc R . . . .
C13 C 0.8472(4) 0.1598(3) 0.8125(3) 0.0236(6) Uani 1 1 d . . . . .
H13 H 0.942266 0.094872 0.798869 0.028 Uiso 1 1 calc R . . . .
C8 C 0.3231(3) 0.4740(3) 0.7839(3) 0.0159(5) Uani 1 1 d . . . . .
C20 C 0.4278(4) -0.1297(3) 0.7541(3) 0.0256(6) Uani 1 1 d . . . . .
H20 H 0.414632 -0.222248 0.788504 0.031 Uiso 1 1 calc R . . . .
C14 C 0.8496(4) 0.2831(3) 0.7401(3) 0.0258(6) Uani 1 1 d . . . . .
H14 H 0.947339 0.302258 0.679220 0.031 Uiso 1 1 calc R . . . .
C6 C -0.0185(4) 0.6563(3) 0.6988(3) 0.0207(6) Uani 1 1 d . . . . .
H6 H -0.047449 0.654186 0.627389 0.025 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 C22 1.893(3) . ?
O1 C7 1.221(3) . ?
N1 C16 1.451(3) . ?
N1 C7 1.393(3) . ?
N1 C8 1.419(3) . ?
C17 C22 1.394(4) . ?
C17 C16 1.518(4) . ?
C17 C18 1.391(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.396(4) . ?
C3 C4 1.389(4) . ?
C22 C21 1.396(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C7 C1 1.485(4) . ?
C2 C1 1.386(4) . ?
C2 C8 1.477(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.400(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.406(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.490(4) . ?
C9 C8 1.347(4) . ?
C10 C11 1.404(4) . ?
C10 C15 1.393(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(4) . ?
C1 C6 1.387(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.392(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.380(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(4) . ?
C20 H20 0.9300 . ?
C14 H14 0.9300 . ?
C6 H6 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
C7 N1 C16 120.1(2) . . ?
C7 N1 C8 111.8(2) . . ?
C8 N1 C16 127.4(2) . . ?
C22 C17 C16 120.7(2) . . ?
C18 C17 C22 117.5(2) . . ?
C18 C17 C16 121.8(2) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C4 C3 C2 117.7(3) . . ?
C17 C22 Br1 120.3(2) . . ?
C17 C22 C21 121.8(3) . . ?
C21 C22 Br1 118.0(2) . . ?
N1 C16 C17 113.7(2) . . ?
N1 C16 H16A 108.8 . . ?
N1 C16 H16B 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
O1 C7 N1 125.0(3) . . ?
O1 C7 C1 128.9(3) . . ?
N1 C7 C1 106.1(2) . . ?
C3 C2 C8 130.7(3) . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 C8 109.4(2) . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.5(3) . . ?
C19 C18 H18 119.2 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.5(3) . . ?
C5 C4 H4 119.2 . . ?
C10 C9 H9 115.7 . . ?
C8 C9 H9 115.7 . . ?
C8 C9 C10 128.6(3) . . ?
C11 C10 C9 119.1(3) . . ?
C15 C10 C9 122.4(2) . . ?
C15 C10 C11 118.5(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C2 C1 C7 107.8(2) . . ?
C2 C1 C6 123.3(3) . . ?
C6 C1 C7 129.0(3) . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C22 C21 H21 120.2 . . ?
C20 C21 C22 119.5(3) . . ?
C20 C21 H21 120.2 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.4(3) . . ?
C20 C19 H19 120.3 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H13 120.2 . . ?
N1 C8 C2 104.9(2) . . ?
C9 C8 N1 130.1(2) . . ?
C9 C8 C2 125.0(3) . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C15 C14 H14 119.8 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.8 . . ?
C1 C6 H6 121.6 . . ?
C5 C6 C1 116.8(3) . . ?
C5 C6 H6 121.6 . . ?

_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 1.171
_oxdiff_exptl_absorpt_empirical_full_min 0.846
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp-188-hks-934-2
_database_code_depnum_ccdc_archive 'CCDC 1853081'
loop_
_audit_author_name
_audit_author_address
'Krishnan Rangan'
;BITS Pilani
India
;
_audit_update_record             
;
2018-07-03 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;
_audit_creation_date             2017-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H21 N O'
_chemical_formula_sum            'C30 H21 N O'
_chemical_formula_weight         411.48
_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'
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                   14.9969(4)
_cell_length_b                   14.8584(3)
_cell_length_c                   10.6249(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.575(3)
_cell_angle_gamma                90
_cell_volume                     2216.53(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5997
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      73.9090
_cell_measurement_theta_min      4.3690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7754
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.409
_diffrn_reflns_theta_min         4.332
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  81.00   0.50    7.00    --    0.00  57.00-180.00  208
  2  ω    -76.00 -50.00   0.50    7.00    --    0.00 -37.00 150.00   52
  3  ω      5.00  31.00   0.50    7.00    --    0.00  57.00 150.00   52
  4  ω    -44.00 -19.00   0.50    7.00    --    0.00 -37.00 150.00   50
  5  ω     52.00 128.00   0.50   28.00    --   95.80 -82.00 -30.00  152
  6  ω     80.00 142.00   0.50   28.00    --   95.80  30.00 -90.00  124
  7  ω     72.00 155.00   0.50   28.00    --   95.80  61.00 120.00  166
  8  ω     27.00  70.00   0.50   28.00    --   95.80 -61.00  30.00   86
  9  ω    108.00 169.00   0.50   28.00    --   95.80  45.00-180.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0863526000
_diffrn_orient_matrix_UB_12      0.0638768000
_diffrn_orient_matrix_UB_13      0.0457670000
_diffrn_orient_matrix_UB_21      -0.0658438000
_diffrn_orient_matrix_UB_22      0.0785451000
_diffrn_orient_matrix_UB_23      0.0046534000
_diffrn_orient_matrix_UB_31      0.0157892000
_diffrn_orient_matrix_UB_32      -0.0223066000
_diffrn_orient_matrix_UB_33      0.1479204000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3723
_reflns_number_total             3961
_reflns_odcompleteness_completeness 92.02
_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 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (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         0.435
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.00093(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3961
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.024
_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)+(0.0477P)²+0.7874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1006
_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:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C9(H9), C11(H11), C19(H19), C3(H3), C15(H15), C20(H20), C21(H21),
 C26(H26), C4(H4), C12(H12), C6(H6), C5(H5), C28(H28), C27(H27), C13(H13),
 C14(H14), C30(H30), C29(H29)
;
_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 0.89236(6) 0.60262(6) 0.68535(9) 0.0324(2) Uani 1 1 d . . . . .
N1 N 0.81347(7) 0.67560(6) 0.48531(10) 0.0241(2) Uani 1 1 d . . . . .
C17 C 0.76128(8) 0.52316(8) 0.38743(11) 0.0238(2) Uani 1 1 d . . . . .
C7 C 0.88004(8) 0.66980(8) 0.61491(12) 0.0259(3) Uani 1 1 d . . . . .
C16 C 0.73687(8) 0.60962(8) 0.44265(12) 0.0241(2) Uani 1 1 d . . . . .
H16A H 0.682390 0.636764 0.374253 0.029 Uiso 1 1 calc R . . . .
H16B H 0.718037 0.595226 0.518813 0.029 Uiso 1 1 calc R . . . .
C2 C 0.88411(8) 0.81428(8) 0.53530(12) 0.0272(3) Uani 1 1 d . . . . .
C8 C 0.81074(8) 0.76339(8) 0.43151(12) 0.0245(2) Uani 1 1 d . . . . .
C1 C 0.92634(8) 0.75863(8) 0.64504(13) 0.0282(3) Uani 1 1 d . . . . .
C10 C 0.68258(9) 0.75301(8) 0.19759(12) 0.0282(3) Uani 1 1 d . . . . .
C18 C 0.85338(9) 0.50095(8) 0.39663(12) 0.0277(3) Uani 1 1 d . . . . .
H18 H 0.902527 0.541769 0.434652 0.033 Uiso 1 1 calc R . . . .
C22 C 0.68758(9) 0.46107(8) 0.32753(12) 0.0279(3) Uani 1 1 d . . . . .
C23 C 0.58979(9) 0.48724(8) 0.30558(13) 0.0304(3) Uani 1 1 d . . . . .
C9 C 0.75242(9) 0.79756(8) 0.31466(12) 0.0276(3) Uani 1 1 d . . . . .
H9 H 0.756854 0.859551 0.306268 0.033 Uiso 1 1 calc R . . . .
C11 C 0.70337(9) 0.67224(9) 0.14711(13) 0.0309(3) Uani 1 1 d . . . . .
H11 H 0.761232 0.643786 0.191075 0.037 Uiso 1 1 calc R . . . .
C25 C 0.41647(9) 0.55163(8) 0.24528(13) 0.0297(3) Uani 1 1 d . . . . .
C19 C 0.87323(9) 0.41868(9) 0.34991(13) 0.0315(3) Uani 1 1 d . . . . .
H19 H 0.934948 0.405581 0.354575 0.038 Uiso 1 1 calc R . . . .
C24 C 0.51208(9) 0.51709(8) 0.28207(14) 0.0320(3) Uani 1 1 d . . . . .
C3 C 0.91189(10) 0.90422(9) 0.53809(14) 0.0346(3) Uani 1 1 d . . . . .
H3 H 0.885562 0.941570 0.464018 0.041 Uiso 1 1 calc R . . . .
C15 C 0.59558(10) 0.79509(10) 0.12849(14) 0.0376(3) Uani 1 1 d . . . . .
H15 H 0.580523 0.849214 0.160211 0.045 Uiso 1 1 calc R . . . .
C20 C 0.80147(10) 0.35638(9) 0.29658(14) 0.0362(3) Uani 1 1 d . . . . .
H20 H 0.815276 0.300493 0.268481 0.043 Uiso 1 1 calc R . . . .
C21 C 0.70875(10) 0.37730(9) 0.28500(15) 0.0363(3) Uani 1 1 d . . . . .
H21 H 0.660431 0.335389 0.248764 0.044 Uiso 1 1 calc R . . . .
C26 C 0.36467(10) 0.54258(10) 0.33054(15) 0.0379(3) Uani 1 1 d . . . . .
H26 H 0.392703 0.515877 0.414414 0.046 Uiso 1 1 calc R . . . .
C4 C 0.98014(10) 0.93578(10) 0.65530(15) 0.0402(3) Uani 1 1 d . . . . .
H4 H 0.998921 0.995715 0.660156 0.048 Uiso 1 1 calc R . . . .
C12 C 0.63906(10) 0.63386(11) 0.03248(14) 0.0398(3) Uani 1 1 d . . . . .
H12 H 0.653511 0.579534 0.000581 0.048 Uiso 1 1 calc R . . . .
C6 C 0.99529(9) 0.78996(10) 0.76251(14) 0.0354(3) Uani 1 1 d . . . . .
H6 H 1.022852 0.752201 0.835742 0.043 Uiso 1 1 calc R . . . .
C5 C 1.02130(10) 0.88000(11) 0.76595(15) 0.0406(3) Uani 1 1 d . . . . .
H5 H 1.066785 0.903298 0.843168 0.049 Uiso 1 1 calc R . . . .
C28 C 0.22953(10) 0.61350(9) 0.16816(15) 0.0390(3) Uani 1 1 d . . . . .
H28 H 0.166954 0.633734 0.141992 0.047 Uiso 1 1 calc R . . . .
C27 C 0.27171(10) 0.57309(10) 0.29122(16) 0.0411(3) Uani 1 1 d . . . . .
H27 H 0.237478 0.566186 0.348550 0.049 Uiso 1 1 calc R . . . .
C13 C 0.55350(11) 0.67603(12) -0.03465(15) 0.0470(4) Uani 1 1 d . . . . .
H13 H 0.510541 0.650222 -0.111965 0.056 Uiso 1 1 calc R . . . .
C14 C 0.53153(11) 0.75654(12) 0.01280(16) 0.0471(4) Uani 1 1 d . . . . .
H14 H 0.473893 0.784923 -0.032683 0.057 Uiso 1 1 calc R . . . .
C30 C 0.37363(12) 0.59331(12) 0.12249(17) 0.0508(4) Uani 1 1 d . . . . .
H30 H 0.407619 0.601006 0.065000 0.061 Uiso 1 1 calc R . . . .
C29 C 0.28060(12) 0.62374(13) 0.08417(17) 0.0558(5) Uani 1 1 d . . . . .
H29 H 0.252499 0.651296 0.000965 0.067 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 C7 1.2221(15) . ?
N1 C7 1.3907(16) . ?
N1 C16 1.4561(14) . ?
N1 C8 1.4190(15) . ?
C17 C16 1.5099(16) . ?
C17 C18 1.3897(16) . ?
C17 C22 1.4083(16) . ?
C7 C1 1.4732(17) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C2 C8 1.4648(16) . ?
C2 C1 1.3876(18) . ?
C2 C3 1.3970(17) . ?
C8 C9 1.3420(17) . ?
C1 C6 1.3916(18) . ?
C10 C9 1.4720(17) . ?
C10 C11 1.3938(18) . ?
C10 C15 1.3996(18) . ?
C18 H18 0.9300 . ?
C18 C19 1.3903(17) . ?
C22 C23 1.4547(17) . ?
C22 C21 1.3982(18) . ?
C23 C24 1.1887(18) . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.3832(19) . ?
C25 C24 1.4415(18) . ?
C25 C26 1.3917(19) . ?
C25 C30 1.382(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.3812(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.390(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.3874(19) . ?
C21 H21 0.9300 . ?
C26 H26 0.9300 . ?
C26 C27 1.3836(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.391(2) . ?
C5 H5 0.9300 . ?
C28 H28 0.9300 . ?
C28 C27 1.374(2) . ?
C28 C29 1.374(2) . ?
C27 H27 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.382(2) . ?
C14 H14 0.9300 . ?
C30 H30 0.9300 . ?
C30 C29 1.385(2) . ?
C29 H29 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
C7 N1 C16 118.68(10) . . ?
C7 N1 C8 111.40(10) . . ?
C8 N1 C16 125.84(10) . . ?
C18 C17 C16 123.06(11) . . ?
C18 C17 C22 118.62(11) . . ?
C22 C17 C16 118.29(10) . . ?
O1 C7 N1 123.94(11) . . ?
O1 C7 C1 129.83(12) . . ?
N1 C7 C1 106.21(10) . . ?
N1 C16 C17 114.91(9) . . ?
N1 C16 H16A 108.5 . . ?
N1 C16 H16B 108.5 . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C1 C2 C8 108.98(11) . . ?
C1 C2 C3 120.50(12) . . ?
C3 C2 C8 130.49(12) . . ?
N1 C8 C2 105.28(10) . . ?
C9 C8 N1 129.62(11) . . ?
C9 C8 C2 125.03(11) . . ?
C2 C1 C7 108.07(11) . . ?
C2 C1 C6 122.02(12) . . ?
C6 C1 C7 129.75(12) . . ?
C11 C10 C9 121.56(11) . . ?
C11 C10 C15 118.44(12) . . ?
C15 C10 C9 119.85(12) . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 121.05(11) . . ?
C19 C18 H18 119.5 . . ?
C17 C22 C23 118.96(11) . . ?
C21 C22 C17 119.87(11) . . ?
C21 C22 C23 121.11(11) . . ?
C24 C23 C22 172.87(14) . . ?
C8 C9 C10 130.58(11) . . ?
C8 C9 H9 114.7 . . ?
C10 C9 H9 114.7 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.85(13) . . ?
C12 C11 H11 119.6 . . ?
C26 C25 C24 121.24(12) . . ?
C30 C25 C24 120.25(12) . . ?
C30 C25 C26 118.50(12) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.14(12) . . ?
C20 C19 H19 119.9 . . ?
C23 C24 C25 176.56(14) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 C2 117.59(13) . . ?
C4 C3 H3 121.2 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.46(14) . . ?
C14 C15 H15 119.8 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.89(12) . . ?
C21 C20 H20 120.1 . . ?
C22 C21 H21 119.8 . . ?
C20 C21 C22 120.33(12) . . ?
C20 C21 H21 119.8 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.36(13) . . ?
C27 C26 H26 119.8 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.68(13) . . ?
C5 C4 H4 119.2 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.12(14) . . ?
C13 C12 H12 119.9 . . ?
C1 C6 H6 121.4 . . ?
C5 C6 C1 117.29(13) . . ?
C5 C6 H6 121.4 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.89(13) . . ?
C6 C5 H5 119.6 . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C29 C28 C27 119.41(13) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.56(13) . . ?
C28 C27 H27 119.7 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.13(14) . . ?
C14 C13 H13 119.9 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.00(14) . . ?
C13 C14 H14 120.0 . . ?
C25 C30 H30 119.7 . . ?
C25 C30 C29 120.67(14) . . ?
C29 C30 H30 119.7 . . ?
C28 C29 C30 120.47(15) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?

_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 1.299
_oxdiff_exptl_absorpt_empirical_full_min 0.733
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_140-hks-900
_database_code_depnum_ccdc_archive 'CCDC 1853630'
loop_
_audit_author_name
_audit_author_address
'Krishnan Rangan'
;BITS Pilani
India
;
_audit_update_record             
;
2018-07-05 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;
_audit_creation_date             2017-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 N O'
_chemical_formula_sum            'C22 H15 N O'
_chemical_formula_weight         309.35
_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                   10.6454(10)
_cell_length_b                   15.8564(11)
_cell_length_c                   9.6081(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.912(12)
_cell_angle_gamma                90
_cell_volume                     1493.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8103
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.7620
_cell_measurement_theta_min      5.2510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10300
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.958
_diffrn_reflns_theta_min         5.025
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -95.00  55.00   0.50   25.00    --   -7.40  19.00 150.00  300
  2  ω     32.00  58.00   0.50   25.00    --   -7.40  57.00 -30.00   52
  3  ω     17.00  44.00   0.50   25.00    --    7.40 -77.00 -30.00   54
  4  ω    -19.00  82.00   0.50   25.00    --    7.40  57.00-180.00  202
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0670761000
_diffrn_orient_matrix_UB_12      0.0058556000
_diffrn_orient_matrix_UB_13      0.0028149000
_diffrn_orient_matrix_UB_21      0.0268907000
_diffrn_orient_matrix_UB_22      -0.0065041000
_diffrn_orient_matrix_UB_23      0.0793232000
_diffrn_orient_matrix_UB_31      0.0045112000
_diffrn_orient_matrix_UB_32      -0.0438393000
_diffrn_orient_matrix_UB_33      -0.0113856000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3232
_reflns_number_total             3477
_reflns_odcompleteness_completeness 98.93
_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 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (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         0.300
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0855
_refine_ls_restrained_S_all      1.058
_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)+(0.0946P)²+3.5579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2156
_refine_ls_wR_factor_ref         0.2174
_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:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C6(H6), C20(H20), C13(H13), C19(H19), C4(H4), C3(H3), C22(H22),
 C5(H5), C14(H14), C16(H16), C18(H18), 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 0.7577(2) 0.40426(13) 0.6879(2) 0.0279(5) Uani 1 1 d . . . . .
N1 N 0.5212(2) 0.39988(13) 0.5973(2) 0.0171(4) Uani 1 1 d . . . . .
C1 C 0.6128(2) 0.36780(15) 0.4245(3) 0.0178(5) Uani 1 1 d . . . . .
C21 C 0.0081(2) 0.38599(15) 0.0517(3) 0.0175(5) Uani 1 1 d . . . . .
H21 H -0.019316 0.420656 -0.033045 0.021 Uiso 1 1 calc R . . . .
C7 C 0.6455(2) 0.39318(15) 0.5830(3) 0.0169(5) Uani 1 1 d . . . . .
C6 C 0.7026(2) 0.35416(16) 0.3541(3) 0.0202(5) Uani 1 1 d . . . . .
H6 H 0.795699 0.363049 0.405420 0.024 Uiso 1 1 calc R . . . .
C20 C -0.0649(2) 0.31331(16) 0.0505(3) 0.0180(5) Uani 1 1 d . . . . .
H20 H -0.142418 0.299917 -0.034062 0.022 Uiso 1 1 calc R . . . .
C2 C 0.4719(2) 0.35539(15) 0.3492(3) 0.0181(5) Uani 1 1 d . . . . .
C13 C 0.3378(3) 0.45009(16) 0.8460(3) 0.0202(5) Uani 1 1 d . . . . .
H13 H 0.409115 0.460610 0.938228 0.024 Uiso 1 1 calc R . . . .
C19 C -0.0221(3) 0.26072(16) 0.1754(3) 0.0206(5) Uani 1 1 d . . . . .
H19 H -0.069490 0.211113 0.173183 0.025 Uiso 1 1 calc R . . . .
C4 C 0.5097(3) 0.31263(16) 0.1299(3) 0.0224(5) Uani 1 1 d . . . . .
H4 H 0.476149 0.293290 0.030672 0.027 Uiso 1 1 calc R . . . .
C3 C 0.4193(3) 0.32688(16) 0.2006(3) 0.0205(5) Uani 1 1 d . . . . .
H3 H 0.326233 0.317536 0.149646 0.025 Uiso 1 1 calc R . . . .
C10 C 0.2585(3) 0.40615(15) 0.5852(3) 0.0188(5) Uani 1 1 d . . . . .
C22 C 0.1228(3) 0.40709(16) 0.1803(3) 0.0198(5) Uani 1 1 d . . . . .
H22 H 0.171835 0.455732 0.181015 0.024 Uiso 1 1 calc R . . . .
C5 C 0.6499(3) 0.32685(16) 0.2051(3) 0.0214(5) Uani 1 1 d . . . . .
H5 H 0.707905 0.317973 0.154996 0.026 Uiso 1 1 calc R . . . .
C11 C 0.3660(2) 0.42281(15) 0.7236(3) 0.0178(5) Uani 1 1 d . . . . .
C14 C 0.2042(3) 0.46171(17) 0.8316(3) 0.0236(6) Uani 1 1 d . . . . .
H14 H 0.186154 0.480222 0.913852 0.028 Uiso 1 1 calc R . . . .
C12 C 0.5124(3) 0.41086(18) 0.7418(3) 0.0214(5) Uani 1 1 d . . . . .
H12A H 0.565679 0.459671 0.792143 0.026 Uiso 1 1 calc R . . . .
H12B H 0.550327 0.361770 0.804328 0.026 Uiso 1 1 calc R . . . .
C16 C 0.1242(3) 0.41816(17) 0.5731(3) 0.0228(5) Uani 1 1 d . . . . .
H16 H 0.052083 0.407367 0.481655 0.027 Uiso 1 1 calc R . . . .
C17 C 0.1641(2) 0.35491(16) 0.3086(3) 0.0210(5) Uani 1 1 d . . . . .
C8 C 0.4114(3) 0.37747(16) 0.4605(3) 0.0212(5) Uani 1 1 d . . . . .
C18 C 0.0911(3) 0.28161(17) 0.3041(3) 0.0242(6) Uani 1 1 d . . . . .
H18 H 0.118181 0.246242 0.387835 0.029 Uiso 1 1 calc R . . . .
C15 C 0.0977(3) 0.44579(18) 0.6950(3) 0.0255(6) Uani 1 1 d . . . . .
H15 H 0.008148 0.453717 0.685429 0.031 Uiso 1 1 calc R . . . .
C9 C 0.2819(3) 0.37826(16) 0.4503(3) 0.0201(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.239(3) . ?
N1 C7 1.386(3) . ?
N1 C12 1.437(3) . ?
N1 C8 1.423(3) . ?
C1 C7 1.480(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.402(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.387(3) . ?
C21 C22 1.399(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.388(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.385(4) . ?
C2 C3 1.390(4) . ?
C2 C8 1.490(4) . ?
C13 H13 0.9300 . ?
C13 C11 1.391(3) . ?
C13 C14 1.387(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.389(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.396(4) . ?
C4 C5 1.400(4) . ?
C3 H3 0.9300 . ?
C10 C11 1.401(4) . ?
C10 C16 1.402(4) . ?
C10 C9 1.480(3) . ?
C22 H22 0.9300 . ?
C22 C17 1.405(4) . ?
C5 H5 0.9300 . ?
C11 C12 1.511(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C16 H16 0.9300 . ?
C16 C15 1.379(4) . ?
C17 C18 1.390(4) . ?
C17 C9 1.494(3) . ?
C8 C9 1.344(4) . ?
C18 H18 0.9300 . ?
C15 H15 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
C7 N1 C12 121.9(2) . . ?
C7 N1 C8 111.2(2) . . ?
C8 N1 C12 125.7(2) . . ?
C6 C1 C7 127.9(2) . . ?
C6 C1 C2 121.9(2) . . ?
C2 C1 C7 110.2(2) . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 119.9(2) . . ?
C22 C21 H21 120.0 . . ?
O1 C7 N1 124.3(2) . . ?
O1 C7 C1 129.9(2) . . ?
N1 C7 C1 105.8(2) . . ?
C1 C6 H6 120.9 . . ?
C1 C6 C5 118.2(2) . . ?
C5 C6 H6 120.9 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 120.0(2) . . ?
C19 C20 H20 120.0 . . ?
C1 C2 C8 105.7(2) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 C8 134.4(2) . . ?
C11 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C14 C13 C11 120.5(2) . . ?
C20 C19 H19 119.8 . . ?
C20 C19 C18 120.4(2) . . ?
C18 C19 H19 119.8 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C2 C3 C4 118.3(2) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C11 C10 C16 118.9(2) . . ?
C11 C10 C9 122.3(2) . . ?
C16 C10 C9 118.8(2) . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C17 120.1(2) . . ?
C17 C22 H22 119.9 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C13 C11 C10 119.7(2) . . ?
C13 C11 C12 119.6(2) . . ?
C10 C11 C12 120.7(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
N1 C12 C11 110.8(2) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C10 C16 H16 119.6 . . ?
C15 C16 C10 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C22 C17 C9 121.2(2) . . ?
C18 C17 C22 119.0(2) . . ?
C18 C17 C9 119.8(2) . . ?
N1 C8 C2 107.0(2) . . ?
C9 C8 N1 121.1(2) . . ?
C9 C8 C2 131.9(2) . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 120.0 . . ?
C10 C9 C17 120.3(2) . . ?
C8 C9 C10 117.1(2) . . ?
C8 C9 C17 122.5(2) . . ?

_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 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.844
