# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_ahhm068
_database_code_depnum_ccdc_archive 'CCDC 1846530'
_audit_update_record             
;
2018-05-31 deposited with the CCDC.
2018-08-14 downloaded from the CCDC.
;
_audit_creation_date             2017-02-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C18 H18 N2 O)'
_chemical_formula_sum            'C36 H36 N4 O2'
_chemical_formula_weight         556.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H30N2O3
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                   22.8586(15)
_cell_length_b                   5.0654(4)
_cell_length_c                   13.0500(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.008(6)
_cell_angle_gamma                90
_cell_volume                     1496.30(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1389
_cell_measurement_temperature    150.03(10)
_cell_measurement_theta_max      28.2740
_cell_measurement_theta_min      4.3150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5349
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.064
_diffrn_reflns_theta_min         3.397
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9881
_diffrn_measured_fraction_theta_max 0.8399
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00 -35.00   1.00   25.00    --  -18.93-178.00   0.00   28
  2  ω      6.00  86.00   1.00   25.00    --   20.02  57.00 -60.00   80
  3  ω     -8.00  83.00   1.00   25.00    --   20.02  19.00  60.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0305120000
_diffrn_orient_matrix_UB_12      0.0205500000
_diffrn_orient_matrix_UB_13      0.0169049000
_diffrn_orient_matrix_UB_21      0.0067899000
_diffrn_orient_matrix_UB_22      -0.0483377000
_diffrn_orient_matrix_UB_23      -0.0479523000
_diffrn_orient_matrix_UB_31      -0.0023202000
_diffrn_orient_matrix_UB_32      0.1298826000
_diffrn_orient_matrix_UB_33      -0.0205383000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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                2129
_reflns_number_total             3345
_reflns_odcompleteness_completeness 98.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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         0.508
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0628
_refine_ls_restrained_S_all      1.023
_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)+(0.0598P)²+0.2763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1540
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008), C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00C(H00D,H00E), C00G(H00H,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 N002(H002), C007(H007), C00A(H00A), C00D(H00F), C00E(H00G), C00H(H00J),
 C00I(H00K), C00J(H00L), C00K(H00M), C00L(H00N)
;
_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
O001 O 0.83557(7) 0.4320(3) 0.54677(10) 0.0402(4) Uani 1 1 d . . . . .
N002 N 0.82184(7) 0.2912(4) 0.24099(12) 0.0256(4) Uani 1 1 d . . . . .
H002 H 0.8040 0.3192 0.1795 0.031 Uiso 1 1 calc R . . . .
N003 N 0.79904(7) 0.1873(4) 0.40765(12) 0.0261(4) Uani 1 1 d . . . . .
C004 C 0.86879(8) 0.4449(4) 0.28448(14) 0.0225(5) Uani 1 1 d . . . . .
C005 C 0.87996(9) 0.4748(4) 0.39225(15) 0.0247(5) Uani 1 1 d . . . . .
C006 C 0.83758(9) 0.3614(4) 0.45623(15) 0.0273(5) Uani 1 1 d . . . . .
C007 C 0.90350(9) 0.5837(4) 0.22320(15) 0.0275(5) Uani 1 1 d . . . . .
H007 H 0.8963 0.5673 0.1516 0.033 Uiso 1 1 calc R . . . .
C008 C 0.80475(9) 0.0820(4) 0.30493(14) 0.0247(5) Uani 1 1 d . . . . .
H008 H 0.8349 -0.0569 0.3113 0.030 Uiso 1 1 calc R . . . .
C009 C 0.74421(9) -0.0392(4) 0.27003(16) 0.0274(5) Uani 1 1 d . . . . .
H009 H 0.7480 -0.1862 0.2226 0.033 Uiso 1 1 calc R . . . .
C00A C 0.92573(9) 0.6369(5) 0.43597(16) 0.0329(6) Uani 1 1 d . . . . .
H00A H 0.9331 0.6557 0.5075 0.039 Uiso 1 1 calc R . . . .
C00B C 0.72793(10) -0.1458(5) 0.37259(16) 0.0325(5) Uani 1 1 d . . . . .
H00B H 0.6854 -0.1622 0.3693 0.039 Uiso 1 1 calc R . . . .
H00C H 0.7458 -0.3174 0.3884 0.039 Uiso 1 1 calc R . . . .
C00C C 0.69915(9) 0.1590(5) 0.21877(17) 0.0315(5) Uani 1 1 d . . . . .
H00D H 0.6915 0.2904 0.2693 0.038 Uiso 1 1 calc R . . . .
H00E H 0.7155 0.2488 0.1636 0.038 Uiso 1 1 calc R . . . .
C00D C 0.94819(9) 0.7441(5) 0.26773(17) 0.0332(5) Uani 1 1 d . . . . .
H00F H 0.9708 0.8371 0.2259 0.040 Uiso 1 1 calc R . . . .
C00E C 0.96032(9) 0.7700(5) 0.37492(18) 0.0360(6) Uani 1 1 d . . . . .
H00G H 0.9914 0.8757 0.4047 0.043 Uiso 1 1 calc R . . . .
C00F C 0.64170(10) 0.0292(5) 0.17488(17) 0.0340(6) Uani 1 1 d . . . . .
C00G C 0.75223(10) 0.0573(5) 0.45408(16) 0.0348(6) Uani 1 1 d . . . . .
H00H H 0.7219 0.1822 0.4668 0.042 Uiso 1 1 calc R . . . .
H00I H 0.7678 -0.0279 0.5187 0.042 Uiso 1 1 calc R . . . .
C00H C 0.59035(10) 0.0722(6) 0.2168(2) 0.0494(7) Uani 1 1 d . . . . .
H00J H 0.5908 0.1850 0.2731 0.059 Uiso 1 1 calc R . . . .
C00I C 0.63913(11) -0.1410(7) 0.0923(2) 0.0569(8) Uani 1 1 d . . . . .
H00K H 0.6732 -0.1745 0.0631 0.068 Uiso 1 1 calc R . . . .
C00J C 0.53828(12) -0.0497(7) 0.1763(3) 0.0670(9) Uani 1 1 d . . . . .
H00L H 0.5040 -0.0174 0.2052 0.080 Uiso 1 1 calc R . . . .
C00K C 0.53672(13) -0.2171(7) 0.0943(3) 0.0759(10) Uani 1 1 d . . . . .
H00M H 0.5016 -0.2996 0.0672 0.091 Uiso 1 1 calc R . . . .
C00L C 0.58720(13) -0.2627(8) 0.0520(3) 0.0815(11) Uani 1 1 d . . . . .
H00N H 0.5865 -0.3764 -0.0041 0.098 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
O001 C006 1.242(2) . ?
N002 H002 0.8600 . ?
N002 C004 1.382(2) . ?
N002 C008 1.436(3) . ?
N003 C006 1.342(3) . ?
N003 C008 1.466(2) . ?
N003 C00G 1.458(3) . ?
C004 C005 1.402(3) . ?
C004 C007 1.393(3) . ?
C005 C006 1.480(3) . ?
C005 C00A 1.389(3) . ?
C007 H007 0.9300 . ?
C007 C00D 1.370(3) . ?
C008 H008 0.9800 . ?
C008 C009 1.524(3) . ?
C009 H009 0.9800 . ?
C009 C00B 1.536(3) . ?
C009 C00C 1.525(3) . ?
C00A H00A 0.9300 . ?
C00A C00E 1.375(3) . ?
C00B H00B 0.9700 . ?
C00B H00C 0.9700 . ?
C00B C00G 1.528(3) . ?
C00C H00D 0.9700 . ?
C00C H00E 0.9700 . ?
C00C C00F 1.509(3) . ?
C00D H00F 0.9300 . ?
C00D C00E 1.394(3) . ?
C00E H00G 0.9300 . ?
C00F C00H 1.379(3) . ?
C00F C00I 1.374(3) . ?
C00G H00H 0.9700 . ?
C00G H00I 0.9700 . ?
C00H H00J 0.9300 . ?
C00H C00J 1.379(4) . ?
C00I H00K 0.9300 . ?
C00I C00L 1.376(4) . ?
C00J H00L 0.9300 . ?
C00J C00K 1.362(4) . ?
C00K H00M 0.9300 . ?
C00K C00L 1.366(4) . ?
C00L H00N 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
C004 N002 H002 122.1 . . ?
C004 N002 C008 115.83(15) . . ?
C008 N002 H002 122.1 . . ?
C006 N003 C008 122.35(16) . . ?
C006 N003 C00G 124.90(17) . . ?
C00G N003 C008 112.31(16) . . ?
N002 C004 C005 119.69(18) . . ?
N002 C004 C007 121.35(17) . . ?
C007 C004 C005 118.86(19) . . ?
C004 C005 C006 118.80(18) . . ?
C00A C005 C004 119.84(19) . . ?
C00A C005 C006 120.84(18) . . ?
O001 C006 N003 122.01(19) . . ?
O001 C006 C005 122.6(2) . . ?
N003 C006 C005 115.27(17) . . ?
C004 C007 H007 119.8 . . ?
C00D C007 C004 120.44(19) . . ?
C00D C007 H007 119.8 . . ?
N002 C008 N003 109.19(17) . . ?
N002 C008 H008 109.5 . . ?
N002 C008 C009 115.64(16) . . ?
N003 C008 H008 109.5 . . ?
N003 C008 C009 103.12(15) . . ?
C009 C008 H008 109.5 . . ?
C008 C009 H009 109.7 . . ?
C008 C009 C00B 101.62(16) . . ?
C008 C009 C00C 113.31(18) . . ?
C00B C009 H009 109.7 . . ?
C00C C009 H009 109.7 . . ?
C00C C009 C00B 112.51(17) . . ?
C005 C00A H00A 119.6 . . ?
C00E C00A C005 120.9(2) . . ?
C00E C00A H00A 119.6 . . ?
C009 C00B H00B 110.7 . . ?
C009 C00B H00C 110.7 . . ?
H00B C00B H00C 108.8 . . ?
C00G C00B C009 105.13(17) . . ?
C00G C00B H00B 110.7 . . ?
C00G C00B H00C 110.7 . . ?
C009 C00C H00D 109.2 . . ?
C009 C00C H00E 109.2 . . ?
H00D C00C H00E 107.9 . . ?
C00F C00C C009 112.26(18) . . ?
C00F C00C H00D 109.2 . . ?
C00F C00C H00E 109.2 . . ?
C007 C00D H00F 119.5 . . ?
C007 C00D C00E 120.9(2) . . ?
C00E C00D H00F 119.5 . . ?
C00A C00E C00D 119.0(2) . . ?
C00A C00E H00G 120.5 . . ?
C00D C00E H00G 120.5 . . ?
C00H C00F C00C 121.6(2) . . ?
C00I C00F C00C 120.7(2) . . ?
C00I C00F C00H 117.6(2) . . ?
N003 C00G C00B 103.39(16) . . ?
N003 C00G H00H 111.1 . . ?
N003 C00G H00I 111.1 . . ?
C00B C00G H00H 111.1 . . ?
C00B C00G H00I 111.1 . . ?
H00H C00G H00I 109.0 . . ?
C00F C00H H00J 119.5 . . ?
C00J C00H C00F 120.9(3) . . ?
C00J C00H H00J 119.5 . . ?
C00F C00I H00K 119.3 . . ?
C00F C00I C00L 121.4(3) . . ?
C00L C00I H00K 119.3 . . ?
C00H C00J H00L 119.8 . . ?
C00K C00J C00H 120.4(3) . . ?
C00K C00J H00L 119.8 . . ?
C00J C00K H00M 120.3 . . ?
C00J C00K C00L 119.4(3) . . ?
C00L C00K H00M 120.3 . . ?
C00I C00L H00N 119.9 . . ?
C00K C00L C00I 120.2(3) . . ?
C00K C00L H00N 119.9 . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.773
_oxdiff_exptl_absorpt_empirical_full_min 0.538
####################################################################### 
# 
# 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_s4650a
_database_code_depnum_ccdc_archive 'CCDC 1846531'
_audit_update_record             
;
2018-05-31 deposited with the CCDC.
2018-08-14 downloaded from the CCDC.
;
_audit_creation_date             2017-03-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 N2 O3'
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.35
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0010(11)
_cell_length_b                   6.9737(7)
_cell_length_c                   20.129(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.637(9)
_cell_angle_gamma                90
_cell_volume                     1541.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2316
_cell_measurement_temperature    149.9(5)
_cell_measurement_theta_max      27.3130
_cell_measurement_theta_min      3.7070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9930
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.342
_diffrn_reflns_theta_min         3.461
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_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    -72.00 -46.00   1.00   50.00    --  -17.61 122.00   8.00   26
  2  ω     29.00  58.00   1.00   50.00    --   19.02 -99.00 -60.00   29
  3  ω    -42.00  28.00   1.00   50.00    --   19.02 -57.00 -90.00   70
  4  ω     20.00  88.00   1.00   50.00    --   19.02  57.00 -30.00   68
  5  ω    -10.00  84.00   1.00   50.00    --   19.02  77.00-120.00   94
  6  ω    -50.00  37.00   1.00   50.00    --   19.02 -57.00-180.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0380531000
_diffrn_orient_matrix_UB_12      0.0094251000
_diffrn_orient_matrix_UB_13      -0.0296111000
_diffrn_orient_matrix_UB_21      -0.0521483000
_diffrn_orient_matrix_UB_22      -0.0027209000
_diffrn_orient_matrix_UB_23      0.0189752000
_diffrn_orient_matrix_UB_31      0.0021279000
_diffrn_orient_matrix_UB_32      0.1012263000
_diffrn_orient_matrix_UB_33      0.0032517000
_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                1996
_reflns_number_total             2826
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.055
_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)+(0.0431P)²+0.0572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1287
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C14(H14), C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 1.14761(16) 0.6537(2) 0.24374(9) 0.0385(5) Uani 1 1 d . . . . .
O2 O 1.02710(16) 0.8746(2) 0.18425(10) 0.0444(6) Uani 1 1 d . . . . .
O3 O 0.39041(15) -0.1373(2) 0.09442(8) 0.0274(5) Uani 1 1 d . . . . .
N1 N 0.50574(17) 0.1303(2) 0.08721(9) 0.0195(5) Uani 1 1 d . . . . .
N2 N 0.42231(17) 0.4401(3) 0.09871(9) 0.0195(5) Uani 1 1 d . . . . .
C1 C 1.1390(2) 0.8514(4) 0.22408(14) 0.0372(7) Uani 1 1 d . . . . .
H1A H 1.1395 0.9349 0.2639 0.045 Uiso 1 1 calc R . . . .
H1B H 1.2091 0.8867 0.1981 0.045 Uiso 1 1 calc R . . . .
C2 C 0.9628(2) 0.7083(3) 0.19207(12) 0.0248(6) Uani 1 1 d . . . . .
C3 C 1.0340(2) 0.5764(3) 0.22772(11) 0.0240(6) Uani 1 1 d . . . . .
C4 C 0.9916(2) 0.3980(4) 0.24095(12) 0.0302(6) Uani 1 1 d . . . . .
H4 H 1.0413 0.3061 0.2646 0.036 Uiso 1 1 calc R . . . .
C5 C 0.8713(2) 0.3557(4) 0.21822(12) 0.0284(6) Uani 1 1 d . . . . .
H5 H 0.8396 0.2320 0.2267 0.034 Uiso 1 1 calc R . . . .
C6 C 0.7974(2) 0.4873(3) 0.18391(11) 0.0230(6) Uani 1 1 d . . . . .
C7 C 0.8455(2) 0.6683(3) 0.16953(12) 0.0271(6) Uani 1 1 d . . . . .
H7 H 0.7978 0.7605 0.1448 0.033 Uiso 1 1 calc R . . . .
C8 C 0.6665(2) 0.4401(4) 0.16203(11) 0.0275(6) Uani 1 1 d . . . . .
H8A H 0.6150 0.5532 0.1700 0.033 Uiso 1 1 calc R . . . .
H8B H 0.6385 0.3337 0.1898 0.033 Uiso 1 1 calc R . . . .
C9 C 0.6486(2) 0.3831(3) 0.08893(11) 0.0225(6) Uani 1 1 d . . . . .
H9 H 0.6778 0.4879 0.0600 0.027 Uiso 1 1 calc R . . . .
C10 C 0.5161(2) 0.3326(3) 0.06815(12) 0.0205(6) Uani 1 1 d . . . . .
H10 H 0.5034 0.3436 0.0187 0.025 Uiso 1 1 calc R . . . .
C11 C 0.3986(2) 0.0395(3) 0.08676(10) 0.0195(6) Uani 1 1 d . . . . .
C12 C 0.2905(2) 0.1666(3) 0.07742(11) 0.0178(5) Uani 1 1 d . . . . .
C13 C 0.3051(2) 0.3664(3) 0.08553(11) 0.0181(5) Uani 1 1 d . . . . .
C14 C 0.2017(2) 0.4829(3) 0.08306(11) 0.0233(6) Uani 1 1 d . . . . .
H14 H 0.2101 0.6172 0.0898 0.028 Uiso 1 1 calc R . . . .
C15 C 0.0874(2) 0.4044(3) 0.07085(12) 0.0283(6) Uani 1 1 d . . . . .
H15 H 0.0178 0.4854 0.0690 0.034 Uiso 1 1 calc R . . . .
C16 C 0.0727(2) 0.2085(3) 0.06124(12) 0.0274(6) Uani 1 1 d . . . . .
H16 H -0.0061 0.1558 0.0517 0.033 Uiso 1 1 calc R . . . .
C17 C 0.1735(2) 0.0918(3) 0.06574(11) 0.0248(6) Uani 1 1 d . . . . .
H17 H 0.1632 -0.0429 0.0608 0.030 Uiso 1 1 calc R . . . .
C18 C 0.6251(2) 0.0370(3) 0.09458(12) 0.0253(6) Uani 1 1 d . . . . .
H18A H 0.6284 -0.0765 0.0652 0.030 Uiso 1 1 calc R . . . .
H18B H 0.6447 -0.0032 0.1412 0.030 Uiso 1 1 calc R . . . .
C19 C 0.7121(2) 0.1943(3) 0.07368(12) 0.0263(6) Uani 1 1 d . . . . .
H19A H 0.7916 0.1846 0.0994 0.032 Uiso 1 1 calc R . . . .
H19B H 0.7256 0.1845 0.0256 0.032 Uiso 1 1 calc R . . . .
H2 H 0.424(2) 0.571(3) 0.0949(11) 0.032 Uiso 1 1 d 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 C1 1.436(3) . ?
O1 C3 1.380(3) . ?
O2 C1 1.435(3) . ?
O2 C2 1.373(3) . ?
O3 C11 1.247(2) . ?
N1 C10 1.468(3) . ?
N1 C11 1.338(3) . ?
N1 C18 1.465(3) . ?
N2 C10 1.444(3) . ?
N2 C13 1.398(3) . ?
N2 H2 0.92(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.380(3) . ?
C2 C7 1.369(3) . ?
C3 C4 1.361(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.404(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(3) . ?
C6 C7 1.406(3) . ?
C6 C8 1.514(3) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.525(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.531(3) . ?
C9 C19 1.531(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.485(3) . ?
C12 C13 1.411(3) . ?
C12 C17 1.395(3) . ?
C13 C14 1.396(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.374(3) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.532(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?

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
C3 O1 C1 105.53(18) . . ?
C2 O2 C1 105.70(18) . . ?
C11 N1 C10 122.42(18) . . ?
C11 N1 C18 125.05(19) . . ?
C18 N1 C10 111.67(18) . . ?
C10 N2 H2 117.5(15) . . ?
C13 N2 C10 113.82(18) . . ?
C13 N2 H2 112.0(15) . . ?
O1 C1 H1A 110.2 . . ?
O1 C1 H1B 110.2 . . ?
O2 C1 O1 107.55(19) . . ?
O2 C1 H1A 110.2 . . ?
O2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
O2 C2 C3 110.1(2) . . ?
C7 C2 O2 128.0(2) . . ?
C7 C2 C3 121.9(2) . . ?
C2 C3 O1 109.7(2) . . ?
C4 C3 O1 128.9(2) . . ?
C4 C3 C2 121.4(2) . . ?
C3 C4 H4 121.4 . . ?
C3 C4 C5 117.1(2) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 H5 118.8 . . ?
C6 C5 C4 122.4(2) . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C7 118.8(2) . . ?
C5 C6 C8 121.3(2) . . ?
C7 C6 C8 119.9(2) . . ?
C2 C7 C6 118.3(2) . . ?
C2 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C6 C8 H8A 108.9 . . ?
C6 C8 H8B 108.9 . . ?
C6 C8 C9 113.6(2) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C8 C9 H9 110.1 . . ?
C8 C9 C10 112.7(2) . . ?
C8 C9 C19 112.64(19) . . ?
C10 C9 H9 110.1 . . ?
C19 C9 H9 110.1 . . ?
C19 C9 C10 100.71(18) . . ?
N1 C10 C9 103.78(18) . . ?
N1 C10 H10 109.0 . . ?
N2 C10 N1 108.53(18) . . ?
N2 C10 C9 117.23(19) . . ?
N2 C10 H10 109.0 . . ?
C9 C10 H10 109.0 . . ?
O3 C11 N1 122.5(2) . . ?
O3 C11 C12 122.8(2) . . ?
N1 C11 C12 114.62(19) . . ?
C13 C12 C11 119.4(2) . . ?
C17 C12 C11 121.4(2) . . ?
C17 C12 C13 119.0(2) . . ?
N2 C13 C12 118.8(2) . . ?
C14 C13 N2 122.2(2) . . ?
C14 C13 C12 119.0(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.2(2) . . ?
C17 C16 H16 120.4 . . ?
C12 C17 H17 119.3 . . ?
C16 C17 C12 121.5(2) . . ?
C16 C17 H17 119.3 . . ?
N1 C18 H18A 111.2 . . ?
N1 C18 H18B 111.2 . . ?
N1 C18 C19 103.01(18) . . ?
H18A C18 H18B 109.1 . . ?
C19 C18 H18A 111.2 . . ?
C19 C18 H18B 111.2 . . ?
C9 C19 C18 105.09(19) . . ?
C9 C19 H19A 110.7 . . ?
C9 C19 H19B 110.7 . . ?
C18 C19 H19A 110.7 . . ?
C18 C19 H19B 110.7 . . ?
H19A C19 H19B 108.8 . . ?

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
O1 C3 C4 C5 -179.4(2) . . . . ?
O2 C2 C3 O1 -0.4(3) . . . . ?
O2 C2 C3 C4 -178.6(2) . . . . ?
O2 C2 C7 C6 -179.5(2) . . . . ?
O3 C11 C12 C13 164.4(2) . . . . ?
O3 C11 C12 C17 -10.7(3) . . . . ?
N1 C11 C12 C13 -14.8(3) . . . . ?
N1 C11 C12 C17 170.1(2) . . . . ?
N1 C18 C19 C9 27.0(2) . . . . ?
N2 C13 C14 C15 -179.1(2) . . . . ?
C1 O1 C3 C2 7.6(3) . . . . ?
C1 O1 C3 C4 -174.3(3) . . . . ?
C1 O2 C2 C3 -7.0(3) . . . . ?
C1 O2 C2 C7 172.9(3) . . . . ?
C2 O2 C1 O1 11.6(3) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C3 O1 C1 O2 -11.8(3) . . . . ?
C3 C2 C7 C6 0.4(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C7 1.9(4) . . . . ?
C4 C5 C6 C8 -177.9(2) . . . . ?
C5 C6 C7 C2 -2.0(4) . . . . ?
C5 C6 C8 C9 -100.1(3) . . . . ?
C6 C8 C9 C10 179.00(19) . . . . ?
C6 C8 C9 C19 65.9(3) . . . . ?
C7 C2 C3 O1 179.7(2) . . . . ?
C7 C2 C3 C4 1.5(4) . . . . ?
C7 C6 C8 C9 80.1(3) . . . . ?
C8 C6 C7 C2 177.8(2) . . . . ?
C8 C9 C10 N1 -84.5(2) . . . . ?
C8 C9 C10 N2 35.1(3) . . . . ?
C8 C9 C19 C18 81.4(2) . . . . ?
C10 N1 C11 O3 170.4(2) . . . . ?
C10 N1 C11 C12 -10.4(3) . . . . ?
C10 N1 C18 C19 -3.8(2) . . . . ?
C10 N2 C13 C12 32.3(3) . . . . ?
C10 N2 C13 C14 -150.6(2) . . . . ?
C10 C9 C19 C18 -38.9(2) . . . . ?
C11 N1 C10 N2 44.1(3) . . . . ?
C11 N1 C10 C9 169.5(2) . . . . ?
C11 N1 C18 C19 165.8(2) . . . . ?
C11 C12 C13 N2 3.4(3) . . . . ?
C11 C12 C13 C14 -173.8(2) . . . . ?
C11 C12 C17 C16 175.9(2) . . . . ?
C12 C13 C14 C15 -2.0(3) . . . . ?
C13 N2 C10 N1 -53.3(2) . . . . ?
C13 N2 C10 C9 -170.38(19) . . . . ?
C13 C12 C17 C16 0.8(3) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C14 C15 C16 C17 1.7(4) . . . . ?
C15 C16 C17 C12 -2.3(4) . . . . ?
C17 C12 C13 N2 178.6(2) . . . . ?
C17 C12 C13 C14 1.4(3) . . . . ?
C18 N1 C10 N2 -145.99(18) . . . . ?
C18 N1 C10 C9 -20.6(2) . . . . ?
C18 N1 C11 O3 1.8(3) . . . . ?
C18 N1 C11 C12 -179.00(19) . . . . ?
C19 C9 C10 N1 35.8(2) . . . . ?
C19 C9 C10 N2 155.39(19) . . . . ?

_olex2_date_sample_data_collection 2017-03-14
_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 1.545
_oxdiff_exptl_absorpt_empirical_full_min 0.667
####################################################################### 
# 
# 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_adjp201
_database_code_depnum_ccdc_archive 'CCDC 1846532'
_audit_update_record             
;
2018-05-31 deposited with the CCDC.
2018-08-14 downloaded from the CCDC.
;
_audit_creation_date             2017-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 N2 O'
_chemical_formula_sum            'C19 H20 N2 O'
_chemical_formula_weight         292.37
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H30N2O3
_chemical_oxdiff_usercomment     'astl 61 oaw1 aw/stl'
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      orthorhombic
_space_group_IT_number           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   41.133(3)
_cell_length_b                   13.3359(14)
_cell_length_c                   11.1564(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6119.8(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5845
_cell_measurement_temperature    149.9(4)
_cell_measurement_theta_max      26.5890
_cell_measurement_theta_min      3.7410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.040
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    0.635
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_av_unetI/netI     0.1089
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19398
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.136
_diffrn_reflns_theta_min         3.212
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  51.00   1.00   22.50    --   20.18  57.00   0.00   52
  2  ω    -49.00  52.00   1.00   22.50    --   20.18 -77.00  30.00  101
  3  ω    -42.00  52.00   1.00   22.50    --   20.18 -77.00 150.00   94
  4  ω      1.00  82.00   1.00   22.50    --   20.18  37.00 -60.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0169092000
_diffrn_orient_matrix_UB_12      0.0104263000
_diffrn_orient_matrix_UB_13      0.0028203000
_diffrn_orient_matrix_UB_21      -0.0033963000
_diffrn_orient_matrix_UB_22      0.0520813000
_diffrn_orient_matrix_UB_23      0.0029939000
_diffrn_orient_matrix_UB_31      -0.0005942000
_diffrn_orient_matrix_UB_32      -0.0026641000
_diffrn_orient_matrix_UB_33      0.0634021000
_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         0.780
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.786
_reflns_number_gt                4664
_reflns_number_total             7118
_reflns_odcompleteness_completeness 99.63
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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         0.427
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 1268 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         7118
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0785
_refine_ls_restrained_S_all      1.010
_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)+(0.1370P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1996
_refine_ls_wR_factor_ref         0.2542
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B), C00H(H00C,H00E), C00J(H00H,H00J)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C10(H10), C7(H7), C6(H6), C00D(H00D), C00F(H00F), C00I(H00I),
 C00K(H00K), C00L(H00L), C00M(H00M)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.71956(7) 0.3392(2) 0.3958(3) 0.0356(7) Uani 1 1 d . . . . .
N4 N 0.72130(8) 0.5045(3) 0.0981(3) 0.0350(8) Uani 1 1 d . . . . .
H4 H 0.7305 0.5539 0.0620 0.042 Uiso 1 1 calc R . . . .
N003 N 0.73584(8) 0.3570(2) 0.2037(3) 0.0270(8) Uani 1 1 d . . . . .
C004 C 0.69446(9) 0.5167(2) 0.1766(4) 0.0260(9) Uani 1 1 d . . . . .
C005 C 0.71536(9) 0.3768(3) 0.2938(4) 0.0248(8) Uani 1 1 d . . . . .
C10 C 0.80710(9) 0.3842(3) -0.2183(4) 0.0288(9) Uani 1 1 d . . . . .
H10 H 0.7879 0.3535 -0.2423 0.035 Uiso 1 1 calc R . . . .
C7 C 0.67281(10) 0.5982(3) 0.1605(4) 0.0355(10) Uani 1 1 d . . . . .
H7 H 0.6767 0.6444 0.0998 0.043 Uiso 1 1 calc R . . . .
C6 C 0.66236(9) 0.4513(3) 0.3424(4) 0.0311(10) Uani 1 1 d . . . . .
H6 H 0.6584 0.4020 0.3995 0.037 Uiso 1 1 calc R . . . .
C9 C 0.80474(11) 0.4492(3) -0.1251(4) 0.0374(11) Uani 1 1 d . . . . .
C8 C 0.70536(10) 0.3416(3) 0.0099(4) 0.0336(9) Uani 1 1 d . . . . .
H8A H 0.6839 0.3616 0.0338 0.050 Uiso 1 1 calc GR . . . .
H8B H 0.7082 0.2713 0.0253 0.050 Uiso 1 1 calc GR . . . .
H8C H 0.7082 0.3544 -0.0741 0.050 Uiso 1 1 calc GR . . . .
C00B C 0.68997(10) 0.4472(3) 0.2672(4) 0.0289(9) Uani 1 1 d . . . . .
C00C C 0.73157(11) 0.4039(3) 0.0844(3) 0.0305(10) Uani 1 1 d . . . . .
C00D C 0.83443(11) 0.5040(3) -0.1006(4) 0.0384(11) Uani 1 1 d . . . . .
H00D H 0.8342 0.5565 -0.0458 0.046 Uiso 1 1 calc R . . . .
C00E C 0.77409(10) 0.4685(3) -0.0583(4) 0.0344(10) Uani 1 1 d . . . . .
H00A H 0.7762 0.5320 -0.0166 0.041 Uiso 1 1 calc R . . . .
H00B H 0.7565 0.4754 -0.1159 0.041 Uiso 1 1 calc R . . . .
C00F C 0.83380(11) 0.3592(3) -0.2795(4) 0.0364(11) Uani 1 1 d . . . . .
H00F H 0.8330 0.3080 -0.3360 0.044 Uiso 1 1 calc R . . . .
C00G C 0.76537(10) 0.3949(3) 0.0251(4) 0.0338(10) Uani 1 1 d . . . . .
H00G H 0.7643 0.3328 -0.0216 0.041 Uiso 1 1 calc R . . . .
C00H C 0.79021(11) 0.3723(3) 0.1264(4) 0.0403(11) Uani 1 1 d . . . . .
H00C H 0.7985 0.4336 0.1618 0.048 Uiso 1 1 calc R . . . .
H00E H 0.8083 0.3324 0.0971 0.048 Uiso 1 1 calc R . . . .
C00I C 0.64629(9) 0.6098(3) 0.2330(4) 0.0359(10) Uani 1 1 d . . . . .
H00I H 0.6323 0.6640 0.2225 0.043 Uiso 1 1 calc R . . . .
C00J C 0.76922(10) 0.3124(3) 0.2173(5) 0.0416(12) Uani 1 1 d . . . . .
H00H H 0.7691 0.2415 0.1980 0.050 Uiso 1 1 calc R . . . .
H00J H 0.7773 0.3211 0.2984 0.050 Uiso 1 1 calc R . . . .
C00K C 0.64021(11) 0.5363(3) 0.3270(3) 0.0399(11) Uani 1 1 d . . . . .
H00K H 0.6223 0.5434 0.3771 0.048 Uiso 1 1 calc R . . . .
C00L C 0.86339(12) 0.4788(4) -0.1584(5) 0.0557(15) Uani 1 1 d . . . . .
H00L H 0.8828 0.5065 -0.1309 0.067 Uiso 1 1 calc R . . . .
C00M C 0.86430(11) 0.4121(3) -0.2579(5) 0.0530(14) Uani 1 1 d . . . . .
H00M H 0.8827 0.4031 -0.3051 0.064 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
O001 C005 1.255(5) . ?
N4 H4 0.8600 . ?
N4 C004 1.419(5) . ?
N4 C00C 1.415(5) . ?
N003 C005 1.338(5) . ?
N003 C00C 1.481(5) . ?
N003 C00J 1.504(5) . ?
C004 C7 1.416(5) . ?
C004 C00B 1.385(5) . ?
C005 C00B 1.435(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.357(5) . ?
C10 C00F 1.336(6) . ?
C7 H7 0.9300 . ?
C7 C00I 1.367(6) . ?
C6 H6 0.9300 . ?
C6 C00B 1.413(5) . ?
C6 C00K 1.465(6) . ?
C9 C00D 1.449(6) . ?
C9 C00E 1.487(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 C00C 1.595(5) . ?
C00C C00G 1.545(5) . ?
C00D H00D 0.9300 . ?
C00D C00L 1.395(6) . ?
C00E H00A 0.9700 . ?
C00E H00B 0.9700 . ?
C00E C00G 1.399(6) . ?
C00F H00F 0.9300 . ?
C00F C00M 1.459(5) . ?
C00G H00G 0.9800 . ?
C00G C00H 1.553(6) . ?
C00H H00C 0.9700 . ?
C00H H00E 0.9700 . ?
C00H C00J 1.553(6) . ?
C00I H00I 0.9300 . ?
C00I C00K 1.457(6) . ?
C00J H00H 0.9700 . ?
C00J H00J 0.9700 . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00M 1.423(6) . ?
C00M H00M 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
C004 N4 H4 123.0 . . ?
C004 N4 C00C 114.1(3) . . ?
C00C N4 H4 123.0 . . ?
C005 N003 C00C 121.1(3) . . ?
C005 N003 C00J 125.2(4) . . ?
C00C N003 C00J 111.5(3) . . ?
C7 C004 N4 120.0(4) . . ?
C00B C004 N4 118.5(3) . . ?
C00B C004 C7 121.5(4) . . ?
O001 C005 N003 121.0(3) . . ?
O001 C005 C00B 123.3(4) . . ?
N003 C005 C00B 115.6(4) . . ?
C9 C10 H10 116.2 . . ?
C00F C10 H10 116.2 . . ?
C00F C10 C9 127.6(4) . . ?
C004 C7 H7 119.5 . . ?
C00I C7 C004 121.0(4) . . ?
C00I C7 H7 119.5 . . ?
C00B C6 H6 121.3 . . ?
C00B C6 C00K 117.4(4) . . ?
C00K C6 H6 121.3 . . ?
C10 C9 C00D 114.0(4) . . ?
C10 C9 C00E 123.7(4) . . ?
C00D C9 C00E 122.2(4) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C00C C8 H8A 109.5 . . ?
C00C C8 H8B 109.5 . . ?
C00C C8 H8C 109.5 . . ?
C004 C00B C005 119.5(4) . . ?
C004 C00B C6 121.0(4) . . ?
C6 C00B C005 119.2(4) . . ?
N4 C00C N003 109.8(3) . . ?
N4 C00C C8 110.4(4) . . ?
N4 C00C C00G 112.8(3) . . ?
N003 C00C C8 109.2(3) . . ?
N003 C00C C00G 104.2(3) . . ?
C00G C00C C8 110.2(3) . . ?
C9 C00D H00D 119.6 . . ?
C00L C00D C9 120.7(4) . . ?
C00L C00D H00D 119.6 . . ?
C9 C00E H00A 108.4 . . ?
C9 C00E H00B 108.4 . . ?
H00A C00E H00B 107.5 . . ?
C00G C00E C9 115.4(4) . . ?
C00G C00E H00A 108.4 . . ?
C00G C00E H00B 108.4 . . ?
C10 C00F H00F 119.9 . . ?
C10 C00F C00M 120.1(4) . . ?
C00M C00F H00F 119.9 . . ?
C00C C00G H00G 104.6 . . ?
C00C C00G C00H 107.1(3) . . ?
C00E C00G C00C 117.5(4) . . ?
C00E C00G H00G 104.6 . . ?
C00E C00G C00H 116.9(4) . . ?
C00H C00G H00G 104.6 . . ?
C00G C00H H00C 111.3 . . ?
C00G C00H H00E 111.3 . . ?
C00G C00H C00J 102.1(4) . . ?
H00C C00H H00E 109.2 . . ?
C00J C00H H00C 111.3 . . ?
C00J C00H H00E 111.3 . . ?
C7 C00I H00I 120.5 . . ?
C7 C00I C00K 119.1(4) . . ?
C00K C00I H00I 120.5 . . ?
N003 C00J C00H 103.8(3) . . ?
N003 C00J H00H 111.0 . . ?
N003 C00J H00J 111.0 . . ?
C00H C00J H00H 111.0 . . ?
C00H C00J H00J 111.0 . . ?
H00H C00J H00J 109.0 . . ?
C6 C00K H00K 120.1 . . ?
C00I C00K C6 119.9(4) . . ?
C00I C00K H00K 120.1 . . ?
C00D C00L H00L 118.9 . . ?
C00D C00L C00M 122.2(4) . . ?
C00M C00L H00L 118.9 . . ?
C00F C00M H00M 123.0 . . ?
C00L C00M C00F 114.1(4) . . ?
C00L C00M H00M 123.0 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.176 -0.761 1665.8 390.3 ?
2 0.500 -0.393 -0.579 1665.8 390.3 ?


_olex2_date_sample_data_collection 2017-03-25
_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 2.632
_oxdiff_exptl_absorpt_empirical_full_min 0.403
