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

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

data_I
_audit_block_doi                 10.5517/ccdc.csd.cc242lkd
_database_code_depnum_ccdc_archive 'CCDC 1968703'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1107/S2414314621003096 2021
#Added by publCIF



_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_iucr_compatibility_tag          ACTA95
_publcif_datablock.id            {eb6c3fef-7140-49b2-8ad4-7c928d3203e3}

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(2E)-2-[(3,4-dimethoxyphenyl)methylidene]-3,4-dihydronaphthalen-1(2H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 O3'
_chemical_formula_sum            'C19 H18 O3'
_chemical_formula_weight         294.33

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.9229(15)
_cell_length_b                   9.4474(19)
_cell_length_c                   20.875(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1562.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9801
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      28.16

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex3 CMOS Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34283
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.356
_diffrn_reflns_theta_max         28.285
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3886
_reflns_number_gt                3101
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1074P)²+0.3866P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.35(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1195 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3886
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1800
_refine_ls_wR_factor_gt          0.1515
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.6008(3) 0.1479(3) 0.28091(12) 0.0624(7) Uani 1 1 d . . . . .
O3 O 0.8450(3) -0.0282(3) 0.26479(12) 0.0649(7) Uani 1 1 d . . . . .
O1 O 0.9071(4) 0.4782(3) 0.59032(11) 0.0649(7) Uani 1 1 d . . . . .
C13 C 0.7334(4) 0.2526(3) 0.37495(14) 0.0458(6) Uani 1 1 d . . . . .
H13 H 0.644379 0.315256 0.381066 0.055 Uiso 1 1 calc R U . . .
C14 C 0.7278(4) 0.1574(3) 0.32452(14) 0.0464(7) Uani 1 1 d . . . . .
C16 C 0.9976(4) 0.0639(3) 0.35657(16) 0.0519(7) Uani 1 1 d . . . . .
H16 H 1.087221 0.001746 0.350367 0.062 Uiso 1 1 calc R U . . .
C15 C 0.8614(4) 0.0615(3) 0.31555(14) 0.0479(7) Uani 1 1 d . . . . .
C8 C 0.8296(4) 0.4838(3) 0.48040(13) 0.0441(6) Uani 1 1 d . . . . .
C17 C 1.0009(4) 0.1591(3) 0.40715(15) 0.0503(7) Uani 1 1 d . . . . .
H17 H 1.092160 0.158070 0.435149 0.060 Uiso 1 1 calc R U . . .
C6 C 0.8282(4) 0.7030(3) 0.55210(13) 0.0446(6) Uani 1 1 d . . . . .
C12 C 0.8722(4) 0.2556(3) 0.41712(14) 0.0449(6) Uani 1 1 d . . . . .
C5 C 0.8007(4) 0.7892(3) 0.49871(15) 0.0475(7) Uani 1 1 d . . . . .
C11 C 0.8832(4) 0.3505(3) 0.47233(14) 0.0471(7) Uani 1 1 d . . . . .
H11 H 0.936499 0.311604 0.507916 0.057 Uiso 1 1 calc R U . . .
C7 C 0.8610(4) 0.5492(3) 0.54443(13) 0.0467(7) Uani 1 1 d . . . . .
C10 C 0.8113(5) 0.7267(3) 0.43275(15) 0.0533(7) Uani 1 1 d . . . . .
H10A H 0.927775 0.728510 0.418478 0.064 Uiso 1 1 calc R U . . .
H10B H 0.745607 0.784317 0.403441 0.064 Uiso 1 1 calc R U . . .
C9 C 0.7464(4) 0.5751(3) 0.43063(15) 0.0510(7) Uani 1 1 d . . . . .
H9A H 0.625376 0.575024 0.437596 0.061 Uiso 1 1 calc R U . . .
H9B H 0.767737 0.535552 0.388515 0.061 Uiso 1 1 calc R U . . .
C1 C 0.8256(4) 0.7620(4) 0.61349(16) 0.0545(8) Uani 1 1 d . . . . .
H1 H 0.844547 0.704442 0.648899 0.065 Uiso 1 1 calc R U . . .
C4 C 0.7687(4) 0.9330(4) 0.50842(18) 0.0566(8) Uani 1 1 d . . . . .
H4 H 0.748799 0.991456 0.473385 0.068 Uiso 1 1 calc R U . . .
C2 C 0.7953(5) 0.9042(4) 0.62230(18) 0.0616(9) Uani 1 1 d . . . . .
H2 H 0.794300 0.942688 0.663314 0.074 Uiso 1 1 calc R U . . .
C3 C 0.7665(5) 0.9893(4) 0.5695(2) 0.0636(9) Uani 1 1 d . . . . .
H3 H 0.745332 1.085375 0.575098 0.076 Uiso 1 1 calc R U . . .
C18 C 0.4641(5) 0.2440(5) 0.2858(2) 0.0755(12) Uani 1 1 d . . . . .
H18A H 0.384295 0.225412 0.252249 0.113 Uiso 1 1 calc R U . . .
H18B H 0.410051 0.232675 0.326635 0.113 Uiso 1 1 calc R U . . .
H18C H 0.505437 0.339161 0.281840 0.113 Uiso 1 1 calc R U . . .
C19 C 0.9838(8) -0.1150(5) 0.2497(3) 0.0900(15) Uani 1 1 d . . . . .
H19A H 0.956607 -0.172841 0.213369 0.135 Uiso 1 1 calc R U . . .
H19B H 1.079682 -0.056856 0.239872 0.135 Uiso 1 1 calc R U . . .
H19C H 1.009656 -0.174440 0.285713 0.135 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C14 1.360(4) . ?
O2 C18 1.417(4) . ?
O3 C15 1.363(4) . ?
O3 C19 1.407(5) . ?
O1 C7 1.225(4) . ?
C13 C14 1.385(4) . ?
C13 C12 1.409(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.406(4) . ?
C16 C15 1.378(5) . ?
C16 C17 1.388(4) . ?
C16 H16 0.9300 . ?
C8 C11 1.340(4) . ?
C8 C7 1.493(4) . ?
C8 C9 1.502(4) . ?
C17 C12 1.383(4) . ?
C17 H17 0.9300 . ?
C6 C5 1.397(4) . ?
C6 C1 1.398(4) . ?
C6 C7 1.485(4) . ?
C12 C11 1.463(4) . ?
C5 C4 1.397(4) . ?
C5 C10 1.500(4) . ?
C11 H11 0.9300 . ?
C10 C9 1.523(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C1 C2 1.377(5) . ?
C1 H1 0.9300 . ?
C4 C3 1.381(5) . ?
C4 H4 0.9300 . ?
C2 C3 1.384(6) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O2 C18 118.3(3) . . ?
C15 O3 C19 117.5(3) . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
O2 C14 C13 125.1(3) . . ?
O2 C14 C15 115.2(3) . . ?
C13 C14 C15 119.7(3) . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
O3 C15 C16 124.6(3) . . ?
O3 C15 C14 115.6(3) . . ?
C16 C15 C14 119.8(3) . . ?
C11 C8 C7 116.6(3) . . ?
C11 C8 C9 126.3(3) . . ?
C7 C8 C9 117.0(3) . . ?
C12 C17 C16 121.9(3) . . ?
C12 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 C7 120.8(2) . . ?
C1 C6 C7 119.5(3) . . ?
C17 C12 C13 117.9(3) . . ?
C17 C12 C11 118.6(3) . . ?
C13 C12 C11 123.5(3) . . ?
C4 C5 C6 118.6(3) . . ?
C4 C5 C10 121.7(3) . . ?
C6 C5 C10 119.6(3) . . ?
C8 C11 C12 131.0(3) . . ?
C8 C11 H11 114.5 . . ?
C12 C11 H11 114.5 . . ?
O1 C7 C6 120.2(3) . . ?
O1 C7 C8 121.5(3) . . ?
C6 C7 C8 118.2(2) . . ?
C5 C10 C9 112.2(3) . . ?
C5 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C5 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C8 C9 C10 111.8(3) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 O2 C14 C13 1.5(5) . . . . ?
C18 O2 C14 C15 -178.2(3) . . . . ?
C12 C13 C14 O2 -179.0(3) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C19 O3 C15 C16 -6.3(5) . . . . ?
C19 O3 C15 C14 173.1(4) . . . . ?
C17 C16 C15 O3 -179.5(3) . . . . ?
C17 C16 C15 C14 1.1(5) . . . . ?
O2 C14 C15 O3 -0.4(4) . . . . ?
C13 C14 C15 O3 179.9(3) . . . . ?
O2 C14 C15 C16 179.0(3) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C15 C16 C17 C12 -1.6(5) . . . . ?
C16 C17 C12 C13 1.6(5) . . . . ?
C16 C17 C12 C11 178.7(3) . . . . ?
C14 C13 C12 C17 -1.1(4) . . . . ?
C14 C13 C12 C11 -178.1(3) . . . . ?
C1 C6 C5 C4 -0.9(5) . . . . ?
C7 C6 C5 C4 179.4(3) . . . . ?
C1 C6 C5 C10 177.3(3) . . . . ?
C7 C6 C5 C10 -2.4(4) . . . . ?
C7 C8 C11 C12 179.4(3) . . . . ?
C9 C8 C11 C12 -2.8(6) . . . . ?
C17 C12 C11 C8 147.4(3) . . . . ?
C13 C12 C11 C8 -35.7(5) . . . . ?
C5 C6 C7 O1 170.2(3) . . . . ?
C1 C6 C7 O1 -9.5(5) . . . . ?
C5 C6 C7 C8 -12.2(4) . . . . ?
C1 C6 C7 C8 168.1(3) . . . . ?
C11 C8 C7 O1 -11.9(5) . . . . ?
C9 C8 C7 O1 170.1(3) . . . . ?
C11 C8 C7 C6 170.6(3) . . . . ?
C9 C8 C7 C6 -7.4(4) . . . . ?
C4 C5 C10 C9 -146.9(3) . . . . ?
C6 C5 C10 C9 35.0(4) . . . . ?
C11 C8 C9 C10 -138.6(3) . . . . ?
C7 C8 C9 C10 39.2(4) . . . . ?
C5 C10 C9 C8 -52.3(4) . . . . ?
C5 C6 C1 C2 0.4(5) . . . . ?
C7 C6 C1 C2 -179.9(3) . . . . ?
C6 C5 C4 C3 0.8(5) . . . . ?
C10 C5 C4 C3 -177.3(3) . . . . ?
C6 C1 C2 C3 0.3(6) . . . . ?
C5 C4 C3 C2 -0.2(5) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O3 0.93 2.52 3.385(4) 155 2_665 yes

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.054


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;

####################################################################### 
# 
# 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_aeb-28
_database_code_depnum_ccdc_archive 'CCDC 1969714'
loop_
_audit_author_name
_audit_author_address
'Ramendra Pratap'
;University of Delhi
India
;
_audit_update_record             
;
2019-12-03 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_audit_creation_date             2019-11-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        'conjugated triene'
_chemical_formula_moiety         'C20 H22 N2'
_chemical_formula_sum            'C20 H22 N2'
_chemical_formula_weight         290.39
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H22 N2 O2'
_chemical_oxdiff_usercomment     25-01-2018
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'

_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   6.2510(2)
_cell_length_b                   18.8202(6)
_cell_length_c                   14.2270(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.706(3)
_cell_angle_gamma                90
_cell_volume                     1654.45(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3697
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5470
_cell_measurement_theta_min      3.9350
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86589
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11420
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.096
_diffrn_reflns_theta_min         3.470
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9853
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  88.00   1.00    3.50    --   19.15  57.00   0.00   83
  2  ω      3.00  88.00   1.00    3.50    --   19.15  57.00 -90.00   85
  3  ω      7.00  88.00   1.00    3.50    --   19.15  57.00-180.00   81
  4  ω    -25.00  60.00   1.00    3.50    --   19.15 -99.00-150.00   85
  5  ω    -21.00  60.00   1.00    3.50    --   19.15 -99.00  30.00   81
  6  ω    -25.00  56.00   1.00    3.50    --   19.15 -99.00 120.00   81
  7  ω      4.00  78.00   1.00    3.50    --   19.15  57.00  90.00   74
  8  ω    -47.00  37.00   1.00    3.50    --   19.15 -38.00-120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0172032000
_diffrn_orient_matrix_UB_12      -0.0372345000
_diffrn_orient_matrix_UB_13      -0.0008593000
_diffrn_orient_matrix_UB_21      0.0071682000
_diffrn_orient_matrix_UB_22      0.0018831000
_diffrn_orient_matrix_UB_23      -0.0492294000
_diffrn_orient_matrix_UB_31      0.1132440000
_diffrn_orient_matrix_UB_32      0.0055243000
_diffrn_orient_matrix_UB_33      0.0109844000
_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         0.994
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3167
_reflns_number_total             3615
_reflns_odcompleteness_completeness 99.77
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3615
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0761
_refine_ls_restrained_S_all      1.082
_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)+(0.0982P)²+1.6368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2068
_refine_ls_wR_factor_ref         0.2139
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_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:
 C7(H7A,H7B), C8(H8A,H8B), C20(H20A,H20B), C18(H18A,H18B), C17(H17A,H17B),
 C19(H19A,H19B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C2(H2), C3(H3), C4(H4)
2.c X=CH2 refined with riding coordinates:
 C12(H12A,H12B)
;
_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
C7 C 0.4959(8) 0.1115(3) 0.0806(4) 0.0630(14) Uani 1 1 d . . . . .
H7A H 0.589826 0.075826 0.059192 0.076 Uiso 1 1 calc R . . . .
H7B H 0.585658 0.150075 0.109366 0.076 Uiso 1 1 calc R . . . .
C14 C -0.0453(9) 0.2388(4) -0.1098(5) 0.0703(17) Uani 1 1 d . . . . .
C11 C -0.0357(8) 0.2296(3) 0.1498(4) 0.0584(12) Uani 1 1 d . . . . .
H11 H -0.115068 0.258190 0.103784 0.070 Uiso 1 1 calc R . . . .
C12 C -0.0675(11) 0.2410(4) 0.2372(5) 0.0769(17) Uani 1 1 d . . . . .
H12A H 0.006944 0.214185 0.286607 0.092 Uiso 1 1 calc R . . . .
H12B H -0.164516 0.275796 0.250080 0.092 Uiso 1 1 calc R . . . .
C8 C 0.3406(9) 0.1392(3) -0.0035(4) 0.0650(14) Uani 1 1 d . . . . .
H8A H 0.264331 0.099784 -0.037509 0.078 Uiso 1 1 calc R . . . .
H8B H 0.420349 0.164052 -0.046866 0.078 Uiso 1 1 calc R . . . .
C1 C 0.1792(7) 0.1121(2) 0.1681(3) 0.0440(10) Uani 1 1 d . . . . .
C10 C 0.1088(7) 0.1778(2) 0.1144(3) 0.0459(10) Uani 1 1 d . . . . .
C5 C 0.4420(9) 0.0180(3) 0.2023(4) 0.0584(12) Uani 1 1 d . . . . .
H5 H 0.573236 -0.002557 0.194166 0.070 Uiso 1 1 calc R . . . .
C6 C 0.3729(7) 0.0798(2) 0.1521(3) 0.0481(10) Uani 1 1 d . . . . .
C2 C 0.0547(8) 0.0792(3) 0.2282(4) 0.0551(12) Uani 1 1 d . . . . .
H2 H -0.076950 0.099133 0.236993 0.066 Uiso 1 1 calc R . . . .
C9 C 0.1798(7) 0.1893(3) 0.0316(4) 0.0516(11) Uani 1 1 d . . . . .
N1 N 0.1957(9) 0.3142(3) -0.0104(5) 0.095(2) Uani 1 1 d . . . . .
C3 C 0.1244(11) 0.0164(3) 0.2756(4) 0.0691(16) Uani 1 1 d . . . . .
H3 H 0.039188 -0.005425 0.315380 0.083 Uiso 1 1 calc R . . . .
C13 C 0.1069(8) 0.2505(3) -0.0330(4) 0.0622(14) Uani 1 1 d . . . . .
C4 C 0.3192(10) -0.0127(3) 0.2633(4) 0.0654(15) Uani 1 1 d . . . . .
H4 H 0.368224 -0.053588 0.296449 0.078 Uiso 1 1 calc R . . . .
C20 C 0.1277(16) 0.3773(5) -0.0674(10) 0.154(6) Uani 1 1 d . . . . .
H20A H 0.166294 0.370144 -0.130237 0.185 Uiso 1 1 calc R . . . .
H20B H -0.028865 0.380038 -0.074768 0.185 Uiso 1 1 calc R . . . .
C18 C 0.4284(15) 0.4448(4) 0.0217(6) 0.097(2) Uani 1 1 d . . . . .
H18A H 0.534571 0.452264 -0.020519 0.117 Uiso 1 1 calc R . . . .
H18B H 0.431678 0.485624 0.063464 0.117 Uiso 1 1 calc R . . . .
C17 C 0.4843(17) 0.3787(4) 0.0798(8) 0.129(4) Uani 1 1 d . . . . .
H17A H 0.640539 0.373710 0.089017 0.154 Uiso 1 1 calc R . . . .
H17B H 0.443470 0.386874 0.142049 0.154 Uiso 1 1 calc R . . . .
C19 C 0.204(2) 0.4376(4) -0.0366(9) 0.157(6) Uani 1 1 d . . . . .
H19A H 0.102111 0.457436 0.001400 0.188 Uiso 1 1 calc R . . . .
H19B H 0.200873 0.468248 -0.091635 0.188 Uiso 1 1 calc R . . . .
C16 C 0.4056(18) 0.3203(5) 0.0507(12) 0.209(9) Uani 1 1 d . . . . .
H16A H 0.397134 0.291530 0.106574 0.251 Uiso 1 1 calc R . . . .
H16B H 0.511060 0.297709 0.017007 0.251 Uiso 1 1 calc R . . . .
N2 N -0.2215(10) 0.1167(3) -0.1407(5) 0.0863(16) Uani 1 1 d . . . . .
C15 C -0.1404(9) 0.1707(4) -0.1263(4) 0.0630(13) Uani 1 1 d . . . . .
H14 H -0.072(13) 0.268(4) -0.157(5) 0.08(2) Uiso 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
C7 C8 1.514(8) . ?
C7 C6 1.490(7) . ?
C14 C13 1.354(8) . ?
C14 C15 1.416(9) . ?
C11 C12 1.307(9) . ?
C11 C10 1.469(7) . ?
C8 C9 1.518(7) . ?
C1 C10 1.485(6) . ?
C1 C6 1.404(6) . ?
C1 C2 1.386(7) . ?
C10 C9 1.338(6) . ?
C5 C6 1.398(6) . ?
C5 C4 1.370(8) . ?
C2 C3 1.397(8) . ?
C9 C13 1.500(7) . ?
N1 C13 1.340(7) . ?
N1 C20 1.464(8) . ?
N1 C16 1.465(9) . ?
C3 C4 1.371(9) . ?
C20 C19 1.282(12) . ?
C18 C17 1.506(10) . ?
C18 C19 1.524(12) . ?
C17 C16 1.248(12) . ?
N2 C15 1.141(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C7 C8 110.0(4) . . ?
C13 C14 C15 120.5(5) . . ?
C12 C11 C10 128.6(5) . . ?
C7 C8 C9 109.4(5) . . ?
C6 C1 C10 118.2(4) . . ?
C2 C1 C10 122.6(4) . . ?
C2 C1 C6 119.0(4) . . ?
C11 C10 C1 121.8(4) . . ?
C9 C10 C11 119.8(4) . . ?
C9 C10 C1 118.4(4) . . ?
C4 C5 C6 121.0(5) . . ?
C1 C6 C7 119.0(4) . . ?
C5 C6 C7 122.0(4) . . ?
C5 C6 C1 119.0(4) . . ?
C1 C2 C3 120.8(5) . . ?
C10 C9 C8 120.9(4) . . ?
C10 C9 C13 123.6(5) . . ?
C13 C9 C8 115.5(4) . . ?
C13 N1 C20 121.2(5) . . ?
C13 N1 C16 120.9(5) . . ?
C20 N1 C16 115.1(5) . . ?
C4 C3 C2 119.7(5) . . ?
C14 C13 C9 118.7(5) . . ?
N1 C13 C14 123.7(5) . . ?
N1 C13 C9 117.6(5) . . ?
C5 C4 C3 120.4(5) . . ?
C19 C20 N1 117.9(8) . . ?
C17 C18 C19 110.1(6) . . ?
C16 C17 C18 119.8(8) . . ?
C20 C19 C18 121.9(9) . . ?
C17 C16 N1 122.6(8) . . ?
N2 C15 C14 178.3(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 1.196
_oxdiff_exptl_absorpt_empirical_full_min 0.736
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
