# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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. 
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#######################################################################

data_jb318absbeam
_database_code_depnum_ccdc_archive 'CCDC 2016747'
loop_
_audit_author_name
_audit_author_address
'PROFESSOR J D WALLIS'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2020-07-16 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;
_audit_creation_date             2019-09-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
2-Cyano-3-(6?-(dimethylamino)-1?,2?-dihydroacenaphthylen-5?-yl)propenenitrile
_chemical_formula_moiety         'C18 H15 N3'
_chemical_formula_sum            'C18 H15 N3'
_chemical_formula_weight         273.33
_chemical_melting_point          369-372
_chemical_oxdiff_formula         'C18 H15 N3'
_chemical_oxdiff_usercomment     'Orange Plate'
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      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                   9.8149(4)
_cell_length_b                   9.9853(4)
_cell_length_c                   15.1587(6)
_cell_angle_alpha                84.234(3)
_cell_angle_beta                 78.977(4)
_cell_angle_gamma                80.518(3)
_cell_volume                     1434.64(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2560
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.9350
_cell_measurement_theta_min      2.8400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 11 -8 0.1487
-13 1 -11 0.0639
-5 -12 8 0.1250
4 -2 -19 0.1406
-1 11 14 0.1557
-12 -1 -13 0.0811
12 1 13 0.0811
-2 8 17 0.1905
13 -1 10 0.0623
1 -11 -14 0.1901

_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_min          0.133
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.9900 10.9672 -8.0098 0.1686 -0.9154 -0.2265
-13.0108 0.9826 -11.0015 -1.0129 -0.1960 0.0017
-4.9887 -11.9655 8.0107 -0.1598 0.9642 0.2789
4.0085 -2.0277 -18.9961 0.1042 -0.6542 0.7658
-1.0177 11.0035 13.9879 -0.0260 -0.0193 -1.0213
-12.0070 -1.0173 -12.9992 -0.9465 -0.1885 0.1885
12.0070 1.0173 12.9992 0.9465 0.1885 -0.1885
-2.0148 8.0137 16.9906 -0.0388 0.2527 -0.9765
13.0110 -0.9842 10.0015 1.0030 0.1604 0.0285
1.0177 -11.0035 -13.9879 0.0260 0.0193 1.0213

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11593
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.268
_diffrn_reflns_theta_min         2.567
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00   3.00   1.00   60.00    --  -13.67 -64.00 120.64   83
  2  ω    -80.00 -10.00   1.00   60.00    --  -13.67 -63.00  -8.88   70
  3  ω    -30.00   1.00   1.00   60.00    --  -13.67 -57.00-120.00   31
  4  ω     27.00  53.00   1.00   60.00    --  -13.67  57.00 150.00   26
  5  ω    -68.00   3.00   1.00   60.00    --  -13.67 -57.00  30.00   71
  6  ω    -80.00 -13.00   1.00   60.00    --  -13.67 -60.00-129.89   67
  7  ω    -13.00  30.00   1.00   60.00    --   13.74 -57.00-180.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0687828000
_diffrn_orient_matrix_UB_12      -0.0086540000
_diffrn_orient_matrix_UB_13      0.0099543000
_diffrn_orient_matrix_UB_21      -0.0187995000
_diffrn_orient_matrix_UB_22      -0.0488533000
_diffrn_orient_matrix_UB_23      0.0356860000
_diffrn_orient_matrix_UB_31      0.0214333000
_diffrn_orient_matrix_UB_32      -0.0524551000
_diffrn_orient_matrix_UB_33      -0.0301918000
_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                3884
_reflns_number_total             5911
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5911
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0575
_refine_ls_restrained_S_all      1.011
_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)+(0.0475P)²+0.3945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1393
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C15(H15), C20(H20), C21(H21), C25(H25),
 C26(H26), C33(H33)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.97996(17) 0.36342(16) 0.34047(11) 0.0315(4) Uani 1 1 d . . . . .
N2 N 0.6981(2) -0.02832(18) 0.53735(13) 0.0503(5) Uani 1 1 d . . . . .
N3 N 1.0772(2) -0.15164(19) 0.34577(13) 0.0485(5) Uani 1 1 d . . . . .
C1 C 0.8474(2) 0.45125(19) 0.35207(12) 0.0280(5) Uani 1 1 d . . . . .
C2 C 0.8354(2) 0.5891(2) 0.36074(13) 0.0322(5) Uani 1 1 d . . . . .
H2 H 0.916867 0.626790 0.357645 0.039 Uiso 1 1 calc R . . . .
C3 C 0.7055(2) 0.6756(2) 0.37405(13) 0.0343(5) Uani 1 1 d . . . . .
H3 H 0.701969 0.768149 0.379430 0.041 Uiso 1 1 calc R . . . .
C4 C 0.5850(2) 0.62180(19) 0.37895(12) 0.0288(5) Uani 1 1 d . . . . .
C5 C 0.5957(2) 0.48099(19) 0.37096(11) 0.0254(4) Uani 1 1 d . . . . .
C6 C 0.4632(2) 0.4400(2) 0.38060(12) 0.0286(5) Uani 1 1 d . . . . .
C7 C 0.4563(2) 0.3042(2) 0.37915(13) 0.0325(5) Uani 1 1 d . . . . .
H7 H 0.370075 0.273621 0.386116 0.039 Uiso 1 1 calc R . . . .
C8 C 0.5822(2) 0.2121(2) 0.36691(12) 0.0303(5) Uani 1 1 d . . . . .
H8 H 0.576616 0.120016 0.366888 0.036 Uiso 1 1 calc R . . . .
C9 C 0.7137(2) 0.25067(19) 0.35495(12) 0.0255(4) Uani 1 1 d . . . . .
C10 C 0.7235(2) 0.39222(18) 0.35736(11) 0.0238(4) Uani 1 1 d . . . . .
C11 C 0.4322(2) 0.6832(2) 0.39373(16) 0.0364(5) Uani 1 1 d . . . . .
H11A H 0.406(2) 0.730(2) 0.4505(14) 0.041(6) Uiso 1 1 d . . . . .
H11B H 0.416(2) 0.755(2) 0.3443(14) 0.045(6) Uiso 1 1 d . . . . .
C12 C 0.3518(2) 0.5631(2) 0.39360(16) 0.0361(5) Uani 1 1 d . . . . .
H12A H 0.293(2) 0.577(2) 0.3448(14) 0.043(6) Uiso 1 1 d . . . . .
H12B H 0.284(2) 0.550(2) 0.4507(14) 0.043(6) Uiso 1 1 d . . . . .
C13 C 1.0270(2) 0.3215(2) 0.42580(15) 0.0471(6) Uani 1 1 d . . . . .
H13A H 1.051522 0.398400 0.449195 0.071 Uiso 1 1 calc GR . . . .
H13B H 1.107592 0.252116 0.416551 0.071 Uiso 1 1 calc GR . . . .
H13C H 0.952963 0.286284 0.467961 0.071 Uiso 1 1 calc GR . . . .
C14 C 1.0894(2) 0.4175(2) 0.27379(15) 0.0455(6) Uani 1 1 d . . . . .
H14A H 1.056964 0.439596 0.217487 0.068 Uiso 1 1 calc GR . . . .
H14B H 1.172152 0.350514 0.265703 0.068 Uiso 1 1 calc GR . . . .
H14C H 1.111107 0.498096 0.294366 0.068 Uiso 1 1 calc GR . . . .
C15 C 0.8387(2) 0.14779(19) 0.33730(12) 0.0284(5) Uani 1 1 d . . . . .
H15 H 0.907249 0.164445 0.287643 0.034 Uiso 1 1 calc R . . . .
C16 C 0.8606(2) 0.03097(19) 0.38829(13) 0.0306(5) Uani 1 1 d . . . . .
C17 C 0.7686(2) -0.0008(2) 0.47107(14) 0.0355(5) Uani 1 1 d . . . . .
C18 C 0.9819(2) -0.0703(2) 0.36376(13) 0.0355(5) Uani 1 1 d . . . . .
N4 N 0.49079(17) 1.11897(17) 0.16215(11) 0.0328(4) Uani 1 1 d . . . . .
N5 N 0.4186(2) 1.63400(19) 0.14956(14) 0.0512(5) Uani 1 1 d . . . . .
N6 N 0.8195(2) 1.55155(19) -0.02849(13) 0.0508(6) Uani 1 1 d . . . . .
C19 C 0.6200(2) 1.02883(19) 0.15777(12) 0.0279(5) Uani 1 1 d . . . . .
C20 C 0.6244(2) 0.8892(2) 0.16998(13) 0.0343(5) Uani 1 1 d . . . . .
H20 H 0.539896 0.854574 0.182398 0.041 Uiso 1 1 calc R . . . .
C21 C 0.7494(2) 0.7969(2) 0.16467(13) 0.0351(5) Uani 1 1 d . . . . .
H21 H 0.746858 0.703817 0.174446 0.042 Uiso 1 1 calc R . . . .
C22 C 0.8742(2) 0.84485(19) 0.14510(12) 0.0300(5) Uani 1 1 d . . . . .
C23 C 0.8729(2) 0.98675(19) 0.13263(12) 0.0261(4) Uani 1 1 d . . . . .
C24 C 1.0101(2) 1.0194(2) 0.11161(12) 0.0289(5) Uani 1 1 d . . . . .
C25 C 1.0277(2) 1.1536(2) 0.09749(13) 0.0330(5) Uani 1 1 d . . . . .
H25 H 1.117070 1.178186 0.082403 0.040 Uiso 1 1 calc R . . . .
C26 C 0.9076(2) 1.2535(2) 0.10632(12) 0.0306(5) Uani 1 1 d . . . . .
H26 H 0.920441 1.344437 0.097542 0.037 Uiso 1 1 calc R . . . .
C27 C 0.7711(2) 1.22428(19) 0.12738(12) 0.0261(4) Uani 1 1 d . . . . .
C28 C 0.7497(2) 1.08326(18) 0.14000(11) 0.0255(4) Uani 1 1 d . . . . .
C29 C 1.0233(2) 0.7741(2) 0.13457(16) 0.0375(5) Uani 1 1 d . . . . .
H29A H 1.045(2) 0.719(2) 0.1925(15) 0.051(7) Uiso 1 1 d . . . . .
H29B H 1.044(2) 0.711(2) 0.0888(14) 0.045(6) Uiso 1 1 d . . . . .
C30 C 1.1136(2) 0.8896(2) 0.10859(15) 0.0363(5) Uani 1 1 d . . . . .
H30A H 1.171(2) 0.884(2) 0.0473(15) 0.045(6) Uiso 1 1 d . . . . .
H30B H 1.181(2) 0.892(2) 0.1497(14) 0.046(6) Uiso 1 1 d . . . . .
C31 C 0.4596(2) 1.1688(2) 0.07325(15) 0.0467(6) Uani 1 1 d . . . . .
H31A H 0.541811 1.197500 0.035964 0.070 Uiso 1 1 calc GR . . . .
H31B H 0.384954 1.244503 0.079175 0.070 Uiso 1 1 calc GR . . . .
H31C H 0.431513 1.097350 0.046149 0.070 Uiso 1 1 calc GR . . . .
C32 C 0.3700(2) 1.0676(2) 0.21888(16) 0.0480(6) Uani 1 1 d . . . . .
H32A H 0.347758 0.992842 0.191845 0.072 Uiso 1 1 calc GR . . . .
H32B H 0.290892 1.138861 0.224740 0.072 Uiso 1 1 calc GR . . . .
H32C H 0.391862 1.037186 0.277376 0.072 Uiso 1 1 calc GR . . . .
C33 C 0.6543(2) 1.33389(19) 0.14351(12) 0.0288(5) Uani 1 1 d . . . . .
H33 H 0.578904 1.314428 0.187667 0.035 Uiso 1 1 calc R . . . .
C34 C 0.6413(2) 1.46040(19) 0.10251(13) 0.0301(5) Uani 1 1 d . . . . .
C35 C 0.5171(2) 1.5574(2) 0.12925(14) 0.0356(5) Uani 1 1 d . . . . .
C36 C 0.7425(2) 1.5092(2) 0.02969(14) 0.0357(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
N1 C1 1.435(2) . ?
N1 C13 1.455(3) . ?
N1 C14 1.461(2) . ?
N2 C17 1.143(3) . ?
N3 C18 1.142(3) . ?
C1 C2 1.380(3) . ?
C1 C10 1.422(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.409(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.364(3) . ?
C4 C5 1.408(3) . ?
C4 C11 1.508(3) . ?
C5 C6 1.404(3) . ?
C5 C10 1.404(3) . ?
C6 C7 1.372(3) . ?
C6 C12 1.507(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.408(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(3) . ?
C9 C10 1.437(3) . ?
C9 C15 1.465(3) . ?
C11 H11A 0.99(2) . ?
C11 H11B 1.00(2) . ?
C11 C12 1.540(3) . ?
C12 H12A 1.01(2) . ?
C12 H12B 1.00(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C16 1.343(3) . ?
C16 C17 1.439(3) . ?
C16 C18 1.445(3) . ?
N4 C19 1.424(2) . ?
N4 C31 1.460(3) . ?
N4 C32 1.460(3) . ?
N5 C35 1.142(3) . ?
N6 C36 1.142(2) . ?
C19 C20 1.383(3) . ?
C19 C28 1.434(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.402(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.357(3) . ?
C22 C23 1.409(3) . ?
C22 C29 1.503(3) . ?
C23 C24 1.408(3) . ?
C23 C28 1.410(3) . ?
C24 C25 1.370(3) . ?
C24 C30 1.508(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.408(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.389(3) . ?
C27 C28 1.446(3) . ?
C27 C33 1.451(3) . ?
C29 H29A 1.03(2) . ?
C29 H29B 0.95(2) . ?
C29 C30 1.543(3) . ?
C30 H30A 0.99(2) . ?
C30 H30B 1.00(2) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33 0.9300 . ?
C33 C34 1.348(3) . ?
C34 C35 1.446(3) . ?
C34 C36 1.440(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C13 112.04(16) . . ?
C1 N1 C14 114.03(16) . . ?
C13 N1 C14 111.57(17) . . ?
C2 C1 N1 122.77(18) . . ?
C2 C1 C10 118.98(18) . . ?
C10 C1 N1 118.23(16) . . ?
C1 C2 H2 118.4 . . ?
C1 C2 C3 123.16(19) . . ?
C3 C2 H2 118.4 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.09(18) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 118.34(18) . . ?
C3 C4 C11 132.74(18) . . ?
C5 C4 C11 108.91(18) . . ?
C6 C5 C4 111.73(17) . . ?
C6 C5 C10 124.32(17) . . ?
C10 C5 C4 123.93(18) . . ?
C5 C6 C12 109.04(17) . . ?
C7 C6 C5 118.54(18) . . ?
C7 C6 C12 132.39(19) . . ?
C6 C7 H7 120.7 . . ?
C6 C7 C8 118.66(19) . . ?
C8 C7 H7 120.7 . . ?
C7 C8 H8 118.2 . . ?
C9 C8 C7 123.69(18) . . ?
C9 C8 H8 118.2 . . ?
C8 C9 C10 118.63(17) . . ?
C8 C9 C15 119.47(17) . . ?
C10 C9 C15 121.87(17) . . ?
C1 C10 C9 127.30(18) . . ?
C5 C10 C1 116.50(17) . . ?
C5 C10 C9 116.12(17) . . ?
C4 C11 H11A 110.6(12) . . ?
C4 C11 H11B 109.2(12) . . ?
C4 C11 C12 105.12(17) . . ?
H11A C11 H11B 105.8(17) . . ?
C12 C11 H11A 113.6(12) . . ?
C12 C11 H11B 112.7(12) . . ?
C6 C12 C11 105.17(17) . . ?
C6 C12 H12A 111.5(12) . . ?
C6 C12 H12B 110.5(12) . . ?
C11 C12 H12A 112.2(12) . . ?
C11 C12 H12B 112.9(12) . . ?
H12A C12 H12B 104.8(17) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15 117.9 . . ?
C16 C15 C9 124.16(18) . . ?
C16 C15 H15 117.9 . . ?
C15 C16 C17 123.05(18) . . ?
C15 C16 C18 121.34(18) . . ?
C17 C16 C18 115.60(17) . . ?
N2 C17 C16 178.4(2) . . ?
N3 C18 C16 178.8(2) . . ?
C19 N4 C31 112.70(16) . . ?
C19 N4 C32 115.08(17) . . ?
C31 N4 C32 110.76(18) . . ?
N4 C19 C28 119.57(17) . . ?
C20 C19 N4 121.81(18) . . ?
C20 C19 C28 118.63(18) . . ?
C19 C20 H20 118.2 . . ?
C19 C20 C21 123.6(2) . . ?
C21 C20 H20 118.2 . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.28(19) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C23 118.38(19) . . ?
C21 C22 C29 132.10(19) . . ?
C23 C22 C29 109.51(18) . . ?
C22 C23 C28 124.20(19) . . ?
C24 C23 C22 111.25(18) . . ?
C24 C23 C28 124.55(18) . . ?
C23 C24 C30 109.10(18) . . ?
C25 C24 C23 118.78(18) . . ?
C25 C24 C30 132.12(19) . . ?
C24 C25 H25 120.7 . . ?
C24 C25 C26 118.57(19) . . ?
C26 C25 H25 120.7 . . ?
C25 C26 H26 118.1 . . ?
C27 C26 C25 123.85(19) . . ?
C27 C26 H26 118.1 . . ?
C26 C27 C28 118.60(17) . . ?
C26 C27 C33 119.88(18) . . ?
C28 C27 C33 121.32(18) . . ?
C19 C28 C27 128.54(17) . . ?
C23 C28 C19 115.86(17) . . ?
C23 C28 C27 115.59(17) . . ?
C22 C29 H29A 112.2(12) . . ?
C22 C29 H29B 112.1(13) . . ?
C22 C29 C30 104.82(17) . . ?
H29A C29 H29B 106.0(17) . . ?
C30 C29 H29A 111.6(12) . . ?
C30 C29 H29B 110.3(13) . . ?
C24 C30 C29 105.19(17) . . ?
C24 C30 H30A 109.1(12) . . ?
C24 C30 H30B 109.9(12) . . ?
C29 C30 H30A 112.9(12) . . ?
C29 C30 H30B 114.0(12) . . ?
H30A C30 H30B 105.7(17) . . ?
N4 C31 H31A 109.5 . . ?
N4 C31 H31B 109.5 . . ?
N4 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N4 C32 H32A 109.5 . . ?
N4 C32 H32B 109.5 . . ?
N4 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C27 C33 H33 115.9 . . ?
C34 C33 C27 128.14(19) . . ?
C34 C33 H33 115.9 . . ?
C33 C34 C35 120.15(19) . . ?
C33 C34 C36 124.83(18) . . ?
C36 C34 C35 115.00(17) . . ?
N5 C35 C34 179.3(2) . . ?
N6 C36 C34 177.7(2) . . ?

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
N1 C1 C2 C3 -178.61(18) . . . . ?
N1 C1 C10 C5 178.47(15) . . . . ?
N1 C1 C10 C9 1.9(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C1 C10 C5 0.2(3) . . . . ?
C2 C1 C10 C9 -176.32(17) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 C11 179.0(2) . . . . ?
C3 C4 C5 C6 177.83(17) . . . . ?
C3 C4 C5 C10 -0.6(3) . . . . ?
C3 C4 C11 C12 -178.8(2) . . . . ?
C4 C5 C6 C7 -176.64(17) . . . . ?
C4 C5 C6 C12 1.8(2) . . . . ?
C4 C5 C10 C1 0.3(3) . . . . ?
C4 C5 C10 C9 177.25(17) . . . . ?
C4 C11 C12 C6 1.1(2) . . . . ?
C5 C4 C11 C12 -0.1(2) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C5 C6 C12 C11 -1.7(2) . . . . ?
C6 C5 C10 C1 -177.95(17) . . . . ?
C6 C5 C10 C9 -1.0(3) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C7 C6 C12 C11 176.4(2) . . . . ?
C7 C8 C9 C10 1.7(3) . . . . ?
C7 C8 C9 C15 -176.33(17) . . . . ?
C8 C9 C10 C1 175.85(17) . . . . ?
C8 C9 C10 C5 -0.7(2) . . . . ?
C8 C9 C15 C16 -51.9(3) . . . . ?
C9 C15 C16 C17 -5.7(3) . . . . ?
C9 C15 C16 C18 175.85(18) . . . . ?
C10 C1 C2 C3 -0.5(3) . . . . ?
C10 C5 C6 C7 1.8(3) . . . . ?
C10 C5 C6 C12 -179.76(17) . . . . ?
C10 C9 C15 C16 130.2(2) . . . . ?
C11 C4 C5 C6 -1.1(2) . . . . ?
C11 C4 C5 C10 -179.51(17) . . . . ?
C12 C6 C7 C8 -178.8(2) . . . . ?
C13 N1 C1 C2 82.1(2) . . . . ?
C13 N1 C1 C10 -96.1(2) . . . . ?
C14 N1 C1 C2 -45.8(3) . . . . ?
C14 N1 C1 C10 136.01(18) . . . . ?
C15 C9 C10 C1 -6.2(3) . . . . ?
C15 C9 C10 C5 177.26(16) . . . . ?
N4 C19 C20 C21 178.86(17) . . . . ?
N4 C19 C28 C23 -177.15(16) . . . . ?
N4 C19 C28 C27 1.9(3) . . . . ?
C19 C20 C21 C22 -1.1(3) . . . . ?
C20 C19 C28 C23 2.7(2) . . . . ?
C20 C19 C28 C27 -178.26(18) . . . . ?
C20 C21 C22 C23 1.3(3) . . . . ?
C20 C21 C22 C29 -179.9(2) . . . . ?
C21 C22 C23 C24 -179.14(17) . . . . ?
C21 C22 C23 C28 0.6(3) . . . . ?
C21 C22 C29 C30 177.8(2) . . . . ?
C22 C23 C24 C25 -179.88(17) . . . . ?
C22 C23 C24 C30 0.6(2) . . . . ?
C22 C23 C28 C19 -2.6(3) . . . . ?
C22 C23 C28 C27 178.20(16) . . . . ?
C22 C29 C30 C24 3.4(2) . . . . ?
C23 C22 C29 C30 -3.2(2) . . . . ?
C23 C24 C25 C26 1.2(3) . . . . ?
C23 C24 C30 C29 -2.5(2) . . . . ?
C24 C23 C28 C19 177.13(17) . . . . ?
C24 C23 C28 C27 -2.1(3) . . . . ?
C24 C25 C26 C27 -1.0(3) . . . . ?
C25 C24 C30 C29 178.0(2) . . . . ?
C25 C26 C27 C28 -0.8(3) . . . . ?
C25 C26 C27 C33 174.13(17) . . . . ?
C26 C27 C28 C19 -176.86(18) . . . . ?
C26 C27 C28 C23 2.2(2) . . . . ?
C26 C27 C33 C34 35.9(3) . . . . ?
C27 C33 C34 C35 -178.71(19) . . . . ?
C27 C33 C34 C36 3.1(3) . . . . ?
C28 C19 C20 C21 -1.0(3) . . . . ?
C28 C23 C24 C25 0.3(3) . . . . ?
C28 C23 C24 C30 -179.23(17) . . . . ?
C28 C27 C33 C34 -149.3(2) . . . . ?
C29 C22 C23 C24 1.8(2) . . . . ?
C29 C22 C23 C28 -178.46(17) . . . . ?
C30 C24 C25 C26 -179.3(2) . . . . ?
C31 N4 C19 C20 -100.8(2) . . . . ?
C31 N4 C19 C28 79.0(2) . . . . ?
C32 N4 C19 C20 27.5(3) . . . . ?
C32 N4 C19 C28 -152.67(18) . . . . ?
C33 C27 C28 C19 8.3(3) . . . . ?
C33 C27 C28 C23 -172.67(16) . . . . ?

_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 1.108
_oxdiff_exptl_absorpt_empirical_full_min 0.904
_chemical_compound_source        'slow evaporation from a  methanol solution'
####################################################################### 
# 
# 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_in063abs150k
_database_code_depnum_ccdc_archive 'CCDC 2016751'
loop_
_audit_author_name
_audit_author_address
'PROFESSOR J D WALLIS'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2020-07-16 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;
_audit_creation_date             2019-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
'2-Cyano-3-(8?-dimethylamino-4?-dimethylammonio-naphthalen-1?-yl)propene-nitrile chloride'
_chemical_formula_moiety         'Cl, H O0.5, C18 H19 N4'
_chemical_formula_sum            'C18 H20 Cl N4 O0.50'
_chemical_formula_weight         335.83
_chemical_absolute_configuration .
_chemical_melting_point          440-443
_chemical_oxdiff_formula         'C18 H18 N4 Cl1'
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'
Cl Cl 0.1484 0.1585 '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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   44.3599(14)
_cell_length_b                   22.7723(6)
_cell_length_c                   7.0406(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7112.3(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3805
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      27.9860
_cell_measurement_theta_min      3.5860
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2832
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
57 -13 0 0.1132
15 26 -5 0.1412
22 -27 4 0.1449
-56 14 0 0.0262
28 29 0 0.0470
-13 -13 -9 0.2004
-2 0 10 0.1946
-28 -29 1 0.0645

_exptl_crystal_recrystallization_method 
'Slow evaporation of a methanol solution.'
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.13
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
56.7367 -13.2451 -0.1921 -0.9553 -0.2783 -0.0573
14.6640 25.8286 -5.0602 0.1605 0.0407 -0.9669
22.1362 -27.0106 3.9311 -0.6709 -0.2145 0.7028
-55.7221 14.2396 0.1867 0.9601 0.2609 0.0273
28.4263 28.8448 -0.1518 0.1531 -0.4984 -0.8614
-12.5044 -13.0777 -8.8693 -0.2785 0.9585 -0.0901
-1.5395 0.1694 9.9351 0.2494 -0.8076 0.5373
-28.2806 -28.8292 1.1442 -0.1320 0.4154 0.9132

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -58
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11234
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.276
_diffrn_reflns_theta_min         3.285
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  51.00   1.00   25.00    --  -16.16  57.00 -30.00   84
  2  ω    -83.00   1.00   1.00   25.00    --  -16.16 -57.00 150.00   84
  3  ω    -13.00  88.00   1.00   25.00    --   16.24  19.00 -90.00  101
  4  ω    -33.00  -8.00   1.00   25.00    --  -16.16  57.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0125948000
_diffrn_orient_matrix_UB_12      0.0178414000
_diffrn_orient_matrix_UB_13      0.0228505000
_diffrn_orient_matrix_UB_21      -0.0075757000
_diffrn_orient_matrix_UB_22      -0.0102442000
_diffrn_orient_matrix_UB_23      -0.0822817000
_diffrn_orient_matrix_UB_31      -0.0062870000
_diffrn_orient_matrix_UB_32      -0.0233847000
_diffrn_orient_matrix_UB_33      0.0535023000
_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         0.745
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.844
_reflns_number_gt                3691
_reflns_number_total             4014
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1356 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4014
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.079
_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)+(0.0367P)²+4.1535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0843
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.22725(2) -0.33137(3) -1.22048(11) 0.02669(16) Uani 1 1 d . . . . .
O1 O -0.250000 -0.250000 -1.5598(6) 0.0591(11) Uani 1 2 d S T P . .
H1 H -0.2563(9) -0.2222(16) -1.479(6) 0.068(12) Uiso 1 1 d . . . . .
N1 N -0.18006(5) -0.39998(9) -1.7002(4) 0.0289(5) Uani 1 1 d . . . . .
N2 N -0.20852(5) -0.65960(9) -1.5813(3) 0.0262(5) Uani 1 1 d . . . . .
H2 H -0.227649 -0.655737 -1.649786 0.031 Uiso 1 1 calc R . . . .
N3 N -0.13246(7) -0.30344(10) -1.2132(4) 0.0453(7) Uani 1 1 d . . . . .
N4 N -0.09658(6) -0.47146(12) -1.3872(4) 0.0437(7) Uani 1 1 d . . . . .
C1 C -0.19602(6) -0.45197(10) -1.7598(4) 0.0220(6) Uani 1 1 d . . . . .
C2 C -0.21184(6) -0.45853(11) -1.9239(4) 0.0276(6) Uani 1 1 d . . . . .
H2A H -0.214293 -0.427260 -2.007413 0.033 Uiso 1 1 calc R . . . .
C3 C -0.22444(6) -0.51415(11) -1.9640(5) 0.0301(6) Uani 1 1 d . . . . .
H3 H -0.235789 -0.518970 -2.073932 0.036 Uiso 1 1 calc R . . . .
C4 C -0.22040(6) -0.56111(11) -1.8455(4) 0.0257(6) Uani 1 1 d . . . . .
H4 H -0.228252 -0.597545 -1.878859 0.031 Uiso 1 1 calc R . . . .
C5 C -0.20444(5) -0.55487(11) -1.6730(4) 0.0209(5) Uani 1 1 d . . . . .
C6 C -0.19854(5) -0.59938(10) -1.5357(4) 0.0221(6) Uani 1 1 d . . . . .
C7 C -0.18318(6) -0.58785(11) -1.3733(4) 0.0254(6) Uani 1 1 d . . . . .
H7 H -0.179242 -0.618278 -1.288759 0.030 Uiso 1 1 calc R . . . .
C8 C -0.17304(5) -0.53058(11) -1.3300(4) 0.0243(6) Uani 1 1 d . . . . .
H8 H -0.162859 -0.523384 -1.216885 0.029 Uiso 1 1 calc R . . . .
C9 C -0.17826(5) -0.48574(10) -1.4551(4) 0.0203(5) Uani 1 1 d . . . . .
C10 C -0.19306(5) -0.49835(10) -1.6293(4) 0.0197(5) Uani 1 1 d . . . . .
C11 C -0.15039(8) -0.39560(16) -1.7906(5) 0.0447(8) Uani 1 1 d . . . . .
H11A H -0.140223 -0.432709 -1.781591 0.067 Uiso 1 1 calc GR . . . .
H11B H -0.138672 -0.365999 -1.727489 0.067 Uiso 1 1 calc GR . . . .
H11C H -0.152827 -0.385206 -1.921823 0.067 Uiso 1 1 calc GR . . . .
C12 C -0.19781(9) -0.34538(11) -1.7142(6) 0.0527(10) Uani 1 1 d . . . . .
H12A H -0.200129 -0.334765 -1.845299 0.079 Uiso 1 1 calc GR . . . .
H12B H -0.187550 -0.314437 -1.647883 0.079 Uiso 1 1 calc GR . . . .
H12C H -0.217314 -0.351408 -1.658334 0.079 Uiso 1 1 calc GR . . . .
C13 C -0.18706(7) -0.68933(12) -1.7143(6) 0.0471(9) Uani 1 1 d . . . . .
H13A H -0.183936 -0.664980 -1.823894 0.071 Uiso 1 1 calc GR . . . .
H13B H -0.195322 -0.726385 -1.753288 0.071 Uiso 1 1 calc GR . . . .
H13C H -0.168162 -0.695681 -1.651152 0.071 Uiso 1 1 calc GR . . . .
C14 C -0.21476(7) -0.69750(13) -1.4124(5) 0.0437(9) Uani 1 1 d . . . . .
H14A H -0.196245 -0.705303 -1.346460 0.066 Uiso 1 1 calc GR . . . .
H14B H -0.223537 -0.733874 -1.453558 0.066 Uiso 1 1 calc GR . . . .
H14C H -0.228491 -0.677669 -1.328838 0.066 Uiso 1 1 calc GR . . . .
C15 C -0.17131(6) -0.42317(11) -1.4171(4) 0.0288(7) Uani 1 1 d . . . . .
H15 H -0.1882(6) -0.3985(12) -1.380(4) 0.017(7) Uiso 1 1 d . . . . .
C16 C -0.14327(6) -0.40566(12) -1.3547(4) 0.0275(6) Uani 1 1 d . . . . .
C17 C -0.13783(7) -0.34842(13) -1.2766(4) 0.0317(7) Uani 1 1 d . . . . .
C18 C -0.11746(6) -0.44269(13) -1.3738(4) 0.0299(6) 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
N1 C1 1.442(3) . ?
N1 C11 1.465(4) . ?
N1 C12 1.475(3) . ?
N2 C6 1.476(3) . ?
N2 C13 1.497(4) . ?
N2 C14 1.495(4) . ?
N3 C17 1.142(4) . ?
N4 C18 1.138(4) . ?
C1 C2 1.360(4) . ?
C1 C10 1.406(3) . ?
C2 C3 1.413(4) . ?
C3 C4 1.368(4) . ?
C4 C5 1.413(4) . ?
C5 C6 1.425(3) . ?
C5 C10 1.416(3) . ?
C6 C7 1.357(4) . ?
C7 C8 1.413(4) . ?
C8 C9 1.368(3) . ?
C9 C10 1.420(4) . ?
C9 C15 1.482(3) . ?
C15 C16 1.378(4) . ?
C16 C17 1.435(4) . ?
C16 C18 1.428(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 111.8(2) . . ?
C1 N1 C12 114.3(2) . . ?
C11 N1 C12 113.2(3) . . ?
C6 N2 C13 111.4(2) . . ?
C6 N2 C14 114.8(2) . . ?
C14 N2 C13 110.7(2) . . ?
C2 C1 N1 126.2(2) . . ?
C2 C1 C10 121.4(2) . . ?
C10 C1 N1 112.4(2) . . ?
C1 C2 C3 118.2(2) . . ?
C4 C3 C2 121.8(3) . . ?
C3 C4 C5 120.7(2) . . ?
C4 C5 C6 127.1(2) . . ?
C4 C5 C10 117.2(2) . . ?
C10 C5 C6 115.7(2) . . ?
C5 C6 N2 117.3(2) . . ?
C7 C6 N2 120.9(2) . . ?
C7 C6 C5 121.7(2) . . ?
C6 C7 C8 121.4(2) . . ?
C9 C8 C7 119.7(2) . . ?
C8 C9 C10 118.9(2) . . ?
C8 C9 C15 124.5(3) . . ?
C10 C9 C15 116.5(2) . . ?
C1 C10 C5 120.5(2) . . ?
C1 C10 C9 117.1(2) . . ?
C5 C10 C9 122.4(2) . . ?
C16 C15 C9 121.6(2) . . ?
C15 C16 C17 122.5(2) . . ?
C15 C16 C18 121.5(2) . . ?
C18 C16 C17 116.0(2) . . ?
N3 C17 C16 177.5(3) . . ?
N4 C18 C16 178.7(3) . . ?

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
N1 C1 C2 C3 176.0(2) . . . . ?
N1 C1 C10 C5 -173.2(2) . . . . ?
N1 C1 C10 C9 6.6(3) . . . . ?
N2 C6 C7 C8 178.8(2) . . . . ?
C1 C2 C3 C4 -1.8(4) . . . . ?
C2 C1 C10 C5 5.3(4) . . . . ?
C2 C1 C10 C9 -174.9(2) . . . . ?
C2 C3 C4 C5 2.8(4) . . . . ?
C3 C4 C5 C6 179.8(3) . . . . ?
C3 C4 C5 C10 0.2(4) . . . . ?
C4 C5 C6 N2 3.8(4) . . . . ?
C4 C5 C6 C7 -179.2(3) . . . . ?
C4 C5 C10 C1 -4.1(4) . . . . ?
C4 C5 C10 C9 176.1(2) . . . . ?
C5 C6 C7 C8 1.9(4) . . . . ?
C6 C5 C10 C1 176.2(2) . . . . ?
C6 C5 C10 C9 -3.6(3) . . . . ?
C6 C7 C8 C9 -1.2(4) . . . . ?
C7 C8 C9 C10 -1.9(4) . . . . ?
C7 C8 C9 C15 173.9(2) . . . . ?
C8 C9 C10 C1 -175.5(2) . . . . ?
C8 C9 C10 C5 4.4(4) . . . . ?
C8 C9 C15 C16 51.4(4) . . . . ?
C9 C15 C16 C17 -165.6(3) . . . . ?
C9 C15 C16 C18 17.9(5) . . . . ?
C10 C1 C2 C3 -2.3(4) . . . . ?
C10 C5 C6 N2 -176.6(2) . . . . ?
C10 C5 C6 C7 0.5(4) . . . . ?
C10 C9 C15 C16 -132.7(3) . . . . ?
C11 N1 C1 C2 -81.0(3) . . . . ?
C11 N1 C1 C10 97.3(3) . . . . ?
C12 N1 C1 C2 49.1(4) . . . . ?
C12 N1 C1 C10 -132.5(3) . . . . ?
C13 N2 C6 C5 79.3(3) . . . . ?
C13 N2 C6 C7 -97.8(3) . . . . ?
C14 N2 C6 C5 -153.8(2) . . . . ?
C14 N2 C6 C7 29.1(3) . . . . ?
C15 C9 C10 C1 8.4(3) . . . . ?
C15 C9 C10 C5 -171.8(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.079
_oxdiff_exptl_absorpt_empirical_full_min 0.916
####################################################################### 
# 
# 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_in063abs200k
_database_code_depnum_ccdc_archive 'CCDC 2016750'
loop_
_audit_author_name
_audit_author_address
'PROFESSOR J D WALLIS'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2020-07-16 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;
_audit_creation_date             2019-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
'2-Cyano-3-(8?-dimethylamino-4?-dimethylammonio-naphthalen-1?-yl)propene-nitrile chloride'
_chemical_formula_moiety         'Cl, C18 H19 N4, H O0.5'
_chemical_formula_sum            'C18 H20 Cl N4 O0.50'
_chemical_formula_weight         335.83
_chemical_absolute_configuration .
_chemical_melting_point          440-443
_chemical_oxdiff_formula         'C18 H18 N4 Cl1'
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'
Cl Cl 0.1484 0.1585 '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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   44.405(2)
_cell_length_b                   22.8205(11)
_cell_length_c                   7.0822(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7176.7(8)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3520
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      27.8300
_cell_measurement_theta_min      3.5740
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.909
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2832
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
57 -13 0 0.1132
-56 14 0 0.0262
15 26 -5 0.1412
22 -27 4 0.1449
-28 -29 1 0.0645
28 29 0 0.0470
-11 -13 -9 0.2004
-3 0 10 0.1946

_exptl_crystal_recrystallization_method 
'Slow evaporation from a methanol solution'
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.13
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
57.0113 -13.0064 0.0005 -0.9553 -0.2783 -0.0573
-56.0111 14.0063 -0.0005 0.9601 0.2609 0.0273
15.0038 26.0001 -4.9993 0.1605 0.0407 -0.9669
22.0038 -27.0039 3.9997 -0.6709 -0.2145 0.7028
-28.0063 -28.9975 0.9995 -0.1320 0.4154 0.9132
28.0062 28.9972 0.0004 0.1531 -0.4984 -0.8614
-11.0020 -12.9962 -8.9993 -0.2785 0.9585 -0.0901
-3.0011 -0.0026 9.9990 0.2494 -0.8076 0.5373

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -58
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11343
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.275
_diffrn_reflns_theta_min         3.281
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  51.00   1.00   25.00    --  -16.16  57.00 -30.00   84
  2  ω    -83.00   1.00   1.00   25.00    --  -16.16 -57.00 150.00   84
  3  ω    -13.00  88.00   1.00   25.00    --   16.24  19.00 -90.00  101
  4  ω    -33.00  -8.00   1.00   25.00    --  -16.16  57.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0127436000
_diffrn_orient_matrix_UB_12      0.0175890000
_diffrn_orient_matrix_UB_13      0.0211258000
_diffrn_orient_matrix_UB_21      -0.0072126000
_diffrn_orient_matrix_UB_22      -0.0102191000
_diffrn_orient_matrix_UB_23      -0.0829308000
_diffrn_orient_matrix_UB_31      -0.0063766000
_diffrn_orient_matrix_UB_32      -0.0235470000
_diffrn_orient_matrix_UB_33      0.0518121000
_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         0.746
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.845
_reflns_number_gt                3663
_reflns_number_total             4055
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1295 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.092
_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)+(0.0394P)²+4.8757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.02261(2) 0.08135(3) 0.92168(12) 0.03341(19) Uani 1 1 d . . . . .
N1 N -0.06950(6) 0.35050(10) 0.9409(4) 0.0351(6) Uani 1 1 d . . . . .
N2 N -0.04147(5) 0.09075(10) 1.0612(4) 0.0320(6) Uani 1 1 d . . . . .
H2 H -0.022315 0.094633 0.993584 0.038 Uiso 1 1 calc R . . . .
N3 N -0.11765(8) 0.44592(12) 1.4290(5) 0.0588(9) Uani 1 1 d . . . . .
N4 N -0.15331(7) 0.27853(14) 1.2562(5) 0.0565(9) Uani 1 1 d . . . . .
C1 C -0.05391(6) 0.29819(11) 0.8841(4) 0.0272(6) Uani 1 1 d . . . . .
C2 C -0.03803(7) 0.29122(13) 0.7220(5) 0.0346(7) Uani 1 1 d . . . . .
H2A H -0.035435 0.322385 0.638939 0.042 Uiso 1 1 calc R . . . .
C3 C -0.02551(7) 0.23570(13) 0.6819(5) 0.0381(7) Uani 1 1 d . . . . .
H3 H -0.014264 0.230724 0.572287 0.046 Uiso 1 1 calc R . . . .
C4 C -0.02956(7) 0.18911(13) 0.8005(5) 0.0319(7) Uani 1 1 d . . . . .
H4 H -0.021637 0.152728 0.768400 0.038 Uiso 1 1 calc R . . . .
C5 C -0.04561(6) 0.19556(12) 0.9711(4) 0.0256(6) Uani 1 1 d . . . . .
C6 C -0.05139(6) 0.15086(11) 1.1070(4) 0.0265(6) Uani 1 1 d . . . . .
C7 C -0.06662(6) 0.16209(12) 1.2685(5) 0.0316(7) Uani 1 1 d . . . . .
H7 H -0.070556 0.131629 1.352165 0.038 Uiso 1 1 calc R . . . .
C8 C -0.07666(6) 0.21931(12) 1.3122(4) 0.0295(7) Uani 1 1 d . . . . .
H8 H -0.086705 0.226373 1.425214 0.035 Uiso 1 1 calc R . . . .
C9 C -0.07161(6) 0.26429(11) 1.1884(4) 0.0251(6) Uani 1 1 d . . . . .
C10 C -0.05694(6) 0.25208(12) 1.0149(4) 0.0242(6) Uani 1 1 d . . . . .
C11 C -0.09922(9) 0.35509(19) 0.8533(6) 0.0574(11) Uani 1 1 d . . . . .
H11A H -0.096986 0.365561 0.722779 0.086 Uiso 1 1 calc GR . . . .
H11B H -0.110777 0.384633 0.917060 0.086 Uiso 1 1 calc GR . . . .
H11C H -0.109409 0.318103 0.862586 0.086 Uiso 1 1 calc GR . . . .
C12 C -0.05149(11) 0.40468(13) 0.9265(7) 0.0666(13) Uani 1 1 d . . . . .
H12A H -0.031780 0.397922 0.977738 0.100 Uiso 1 1 calc GR . . . .
H12B H -0.061210 0.435442 0.995972 0.100 Uiso 1 1 calc GR . . . .
H12C H -0.049763 0.415896 0.796271 0.100 Uiso 1 1 calc GR . . . .
C13 C -0.06282(8) 0.06133(14) 0.9279(7) 0.0575(11) Uani 1 1 d . . . . .
H13A H -0.081781 0.055127 0.989868 0.086 Uiso 1 1 calc GR . . . .
H13B H -0.054605 0.024291 0.889415 0.086 Uiso 1 1 calc GR . . . .
H13C H -0.065763 0.085686 0.818944 0.086 Uiso 1 1 calc GR . . . .
C14 C -0.03536(9) 0.05262(15) 1.2283(6) 0.0551(11) Uani 1 1 d . . . . .
H14A H -0.022107 0.072648 1.313708 0.083 Uiso 1 1 calc GR . . . .
H14B H -0.026087 0.016826 1.187134 0.083 Uiso 1 1 calc GR . . . .
H14C H -0.053965 0.043873 1.291292 0.083 Uiso 1 1 calc GR . . . .
C15 C -0.07869(7) 0.32629(12) 1.2311(5) 0.0334(7) Uani 1 1 d . . . . .
H15 H -0.0623(6) 0.3517(12) 1.262(4) 0.018(7) Uiso 1 1 d . . . . .
C16 C -0.10659(7) 0.34365(13) 1.2916(5) 0.0333(7) Uani 1 1 d . . . . .
C17 C -0.11224(7) 0.40089(14) 1.3674(5) 0.0399(8) Uani 1 1 d . . . . .
C18 C -0.13241(7) 0.30676(14) 1.2708(5) 0.0375(8) Uani 1 1 d . . . . .
H1 H 0.0064(12) 0.529(2) 0.168(8) 0.107(18) Uiso 1 1 d . . . . .
O1 O 0.000000 0.500000 0.0836(7) 0.0794(15) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.437(4) . ?
N1 C11 1.462(5) . ?
N1 C12 1.476(4) . ?
N2 C6 1.477(3) . ?
N2 C13 1.497(5) . ?
N2 C14 1.494(4) . ?
N3 C17 1.142(4) . ?
N4 C18 1.135(4) . ?
C1 C2 1.357(4) . ?
C1 C10 1.408(4) . ?
C2 C3 1.412(4) . ?
C3 C4 1.367(4) . ?
C4 C5 1.410(4) . ?
C5 C6 1.425(4) . ?
C5 C10 1.419(4) . ?
C6 C7 1.353(4) . ?
C7 C8 1.414(4) . ?
C8 C9 1.368(4) . ?
C9 C10 1.419(4) . ?
C9 C15 1.481(4) . ?
C15 C16 1.369(4) . ?
C16 C17 1.434(4) . ?
C16 C18 1.430(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 112.1(3) . . ?
C1 N1 C12 114.5(3) . . ?
C11 N1 C12 113.6(3) . . ?
C6 N2 C13 111.5(2) . . ?
C6 N2 C14 114.9(3) . . ?
C14 N2 C13 110.7(3) . . ?
C2 C1 N1 125.8(3) . . ?
C2 C1 C10 121.2(3) . . ?
C10 C1 N1 113.0(3) . . ?
C1 C2 C3 118.7(3) . . ?
C4 C3 C2 121.5(3) . . ?
C3 C4 C5 120.8(3) . . ?
C4 C5 C6 126.5(3) . . ?
C4 C5 C10 117.5(3) . . ?
C10 C5 C6 116.0(3) . . ?
C5 C6 N2 117.6(2) . . ?
C7 C6 N2 120.7(2) . . ?
C7 C6 C5 121.7(2) . . ?
C6 C7 C8 121.2(3) . . ?
C9 C8 C7 120.0(3) . . ?
C8 C9 C10 118.9(2) . . ?
C8 C9 C15 123.5(3) . . ?
C10 C9 C15 117.5(2) . . ?
C1 C10 C5 120.1(3) . . ?
C1 C10 C9 117.8(2) . . ?
C5 C10 C9 122.1(2) . . ?
C16 C15 C9 122.2(3) . . ?
C15 C16 C17 122.6(3) . . ?
C15 C16 C18 121.5(3) . . ?
C18 C16 C17 115.8(3) . . ?
N3 C17 C16 177.8(4) . . ?
N4 C18 C16 178.3(4) . . ?

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
N1 C1 C2 C3 -176.2(3) . . . . ?
N1 C1 C10 C5 173.4(2) . . . . ?
N1 C1 C10 C9 -6.4(4) . . . . ?
N2 C6 C7 C8 -178.9(3) . . . . ?
C1 C2 C3 C4 1.2(5) . . . . ?
C2 C1 C10 C5 -5.7(4) . . . . ?
C2 C1 C10 C9 174.5(3) . . . . ?
C2 C3 C4 C5 -2.2(5) . . . . ?
C3 C4 C5 C6 -179.9(3) . . . . ?
C3 C4 C5 C10 -0.7(4) . . . . ?
C4 C5 C6 N2 -4.3(4) . . . . ?
C4 C5 C6 C7 178.7(3) . . . . ?
C4 C5 C10 C1 4.6(4) . . . . ?
C4 C5 C10 C9 -175.7(3) . . . . ?
C5 C6 C7 C8 -2.0(4) . . . . ?
C6 C5 C10 C1 -176.2(2) . . . . ?
C6 C5 C10 C9 3.6(4) . . . . ?
C6 C7 C8 C9 1.4(4) . . . . ?
C7 C8 C9 C10 1.6(4) . . . . ?
C7 C8 C9 C15 -173.9(3) . . . . ?
C8 C9 C10 C1 175.6(3) . . . . ?
C8 C9 C10 C5 -4.2(4) . . . . ?
C8 C9 C15 C16 -53.0(4) . . . . ?
C9 C15 C16 C17 167.8(3) . . . . ?
C9 C15 C16 C18 -16.6(5) . . . . ?
C10 C1 C2 C3 2.7(4) . . . . ?
C10 C5 C6 N2 176.6(2) . . . . ?
C10 C5 C6 C7 -0.4(4) . . . . ?
C10 C9 C15 C16 131.5(3) . . . . ?
C11 N1 C1 C2 82.3(4) . . . . ?
C11 N1 C1 C10 -96.7(3) . . . . ?
C12 N1 C1 C2 -48.9(5) . . . . ?
C12 N1 C1 C10 132.1(3) . . . . ?
C13 N2 C6 C5 -78.8(4) . . . . ?
C13 N2 C6 C7 98.2(4) . . . . ?
C14 N2 C6 C5 154.2(3) . . . . ?
C14 N2 C6 C7 -28.7(4) . . . . ?
C15 C9 C10 C1 -8.7(4) . . . . ?
C15 C9 C10 C5 171.6(3) . . . . ?

_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 1.076
_oxdiff_exptl_absorpt_empirical_full_min 0.912
####################################################################### 
# 
# 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_jb_staceydintrile100kabs
_database_code_depnum_ccdc_archive 'CCDC 2016748'
loop_
_audit_author_name
_audit_author_address
'PROFESSOR J D WALLIS'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2020-07-16 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;
_audit_creation_date             2019-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
2-Cyano-3-((8?-(dimethylamino)-4?,5?-diphenylnaphthalen-1?-yl)propenenitrile
_chemical_formula_moiety         'C28 H21 N3, C7 H8'
_chemical_formula_sum            'C35 H29 N3'
_chemical_formula_weight         491.61
_chemical_melting_point          411-413
_chemical_oxdiff_formula         'C35 H33 N3'
_chemical_oxdiff_usercomment     'Orange Plate'
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      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                   8.6923(3)
_cell_length_b                   12.6464(5)
_cell_length_c                   12.8192(5)
_cell_angle_alpha                81.716(3)
_cell_angle_beta                 77.638(3)
_cell_angle_gamma                78.624(3)
_cell_volume                     1341.80(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10710
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.9340
_cell_measurement_theta_min      3.4900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 17 2 0.0446
1 -17 -1 0.0084
12 5 7 0.1408
0 -1 -17 0.0366
0 1 18 0.0779
11 8 11 0.1352
-11 -8 -10 0.0992

_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.062
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 17.0000 2.0000 0.8975 0.2552 -0.2747
1.0000 -17.0000 -1.0000 -0.9295 -0.2894 0.1948
12.0000 5.0000 7.0000 -0.1925 -0.0311 -0.9792
-0.0000 -1.0000 -17.0000 -0.2686 0.9041 0.1997
0.0000 1.0000 18.0000 0.2814 -0.9585 -0.2106
11.0000 8.0000 11.0000 0.0574 -0.2049 -0.9983
-11.0000 -8.0000 -10.0000 -0.0446 0.1504 0.9874

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            43402
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         3.170
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -1.00   1.00   45.00    --  -19.81 -63.00 -54.64   86
  2  ω    -86.00   0.00   1.00   45.00    --  -19.81 -65.00-114.15   86
  3  ω    -87.00  -3.00   1.00   45.00    --  -19.81 -57.00  60.00   84
  4  ω    -87.00  -2.00   1.00   45.00    --  -19.81 -60.00  25.62   85
  5  ω    -47.00  40.00   1.00   45.00    --   19.89 -65.00-179.83   87
  6  ω      0.00  86.00   1.00   45.00    --   19.89  65.00-147.97   86
  7  φ    126.00 180.00   1.00   45.00  40.00  19.89   0.00    --    54
  8  ω      0.00  86.00   1.00   45.00    --   19.89  64.00 -33.97   86
  9  ω      0.00  86.00   1.00   45.00    --   19.89  65.00-119.27   86
 10  ω    -37.00  47.00   1.00   45.00    --  -19.81  57.00   0.00   84
 11  ω    -47.00  37.00   1.00   45.00    --   19.89 -57.00 -90.00   84
 12  ω      3.00  87.00   1.00   45.00    --   19.89  57.00 150.00   84
 13  ω    -47.00  40.00   1.00   45.00    --   19.89 -65.00  -1.56   87
 14  ω    -47.00  40.00   1.00   45.00    --   19.89 -65.00-133.82   87
 15  ω    -47.00  37.00   1.00   45.00    --   19.89 -57.00 120.00   84
 16  ω    -47.00  39.00   1.00   45.00    --   19.89 -63.00  78.38   86
 17  ω    -47.00  37.00   1.00   45.00    --   19.89 -57.00 -60.00   84
 18  ω      3.00  87.00   1.00   45.00    --   19.89  57.00  30.00   84
 19  ω    -47.00 -22.00   1.00   45.00    --   19.89 -57.00  90.00   25
 20  ω    -47.00  38.00   1.00   45.00    --   19.89 -62.00  23.56   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0448668000
_diffrn_orient_matrix_UB_12      0.0512877000
_diffrn_orient_matrix_UB_13      0.0127822000
_diffrn_orient_matrix_UB_21      0.0202399000
_diffrn_orient_matrix_UB_22      0.0214176000
_diffrn_orient_matrix_UB_23      -0.0544401000
_diffrn_orient_matrix_UB_31      -0.0690585000
_diffrn_orient_matrix_UB_32      -0.0148803000
_diffrn_orient_matrix_UB_33      -0.0108719000
_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                5540
_reflns_number_total             6656
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         6656
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0727
_refine_ls_restrained_S_all      1.153
_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)+(0.0350P)²+0.9907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1377
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C30(H30),
  C31(H31), C32(H32), C33(H33), C34(H34)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C35(H35A,H35B,H35C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.84497(19) 0.83568(13) 0.77705(13) 0.0192(3) Uani 1 1 d . . . . .
N2 N 0.2966(2) 0.98915(13) 0.78255(14) 0.0247(4) Uani 1 1 d . . . . .
N3 N 0.6548(2) 1.10580(14) 0.51321(14) 0.0246(4) Uani 1 1 d . . . . .
C1 C 0.8529(2) 0.72100(15) 0.80075(14) 0.0156(4) Uani 1 1 d . . . . .
C2 C 0.9716(2) 0.65267(16) 0.84375(15) 0.0194(4) Uani 1 1 d . . . . .
H2 H 1.058215 0.678810 0.855973 0.023 Uiso 1 1 calc R . . . .
C3 C 0.9604(2) 0.54263(15) 0.86909(15) 0.0184(4) Uani 1 1 d . . . . .
H3 H 1.044041 0.496216 0.895258 0.022 Uiso 1 1 calc R . . . .
C4 C 0.8320(2) 0.49930(14) 0.85733(14) 0.0140(4) Uani 1 1 d . . . . .
C5 C 0.7088(2) 0.56777(14) 0.80712(14) 0.0132(3) Uani 1 1 d . . . . .
C6 C 0.5725(2) 0.53454(14) 0.78229(14) 0.0130(3) Uani 1 1 d . . . . .
C7 C 0.4634(2) 0.61055(15) 0.73522(14) 0.0157(4) Uani 1 1 d . . . . .
H7 H 0.370333 0.589852 0.726549 0.019 Uiso 1 1 calc R . . . .
C8 C 0.4863(2) 0.71740(14) 0.69993(14) 0.0151(4) Uani 1 1 d . . . . .
H8 H 0.412227 0.765286 0.665684 0.018 Uiso 1 1 calc R . . . .
C9 C 0.6195(2) 0.75056(14) 0.71650(14) 0.0135(3) Uani 1 1 d . . . . .
C10 C 0.7261(2) 0.67901(14) 0.77611(14) 0.0137(4) Uani 1 1 d . . . . .
C11 C 0.9983(3) 0.87290(18) 0.7359(2) 0.0327(5) Uani 1 1 d . . . . .
H11A H 1.055394 0.866394 0.793522 0.049 Uiso 1 1 calc GR . . . .
H11B H 0.979296 0.947387 0.706253 0.049 Uiso 1 1 calc GR . . . .
H11C H 1.060468 0.829295 0.681123 0.049 Uiso 1 1 calc GR . . . .
C12 C 0.7458(3) 0.89755(16) 0.86309(17) 0.0250(4) Uani 1 1 d . . . . .
H12A H 0.647382 0.870243 0.888205 0.038 Uiso 1 1 calc GR . . . .
H12B H 0.723209 0.972679 0.836115 0.038 Uiso 1 1 calc GR . . . .
H12C H 0.801898 0.890273 0.921320 0.038 Uiso 1 1 calc GR . . . .
C13 C 0.8342(2) 0.38258(14) 0.90040(14) 0.0140(4) Uani 1 1 d . . . . .
C14 C 0.9638(2) 0.30499(16) 0.86144(15) 0.0188(4) Uani 1 1 d . . . . .
H14 H 1.045168 0.326267 0.807324 0.023 Uiso 1 1 calc R . . . .
C15 C 0.9734(2) 0.19649(16) 0.90213(16) 0.0213(4) Uani 1 1 d . . . . .
H15 H 1.060103 0.145592 0.874899 0.026 Uiso 1 1 calc R . . . .
C16 C 0.8534(2) 0.16434(16) 0.98339(16) 0.0211(4) Uani 1 1 d . . . . .
H16 H 0.859020 0.091706 1.010557 0.025 Uiso 1 1 calc R . . . .
C17 C 0.7249(2) 0.24059(16) 1.02415(15) 0.0185(4) Uani 1 1 d . . . . .
H17 H 0.644923 0.219096 1.079199 0.022 Uiso 1 1 calc R . . . .
C18 C 0.7153(2) 0.34896(15) 0.98310(14) 0.0150(4) Uani 1 1 d . . . . .
H18 H 0.628701 0.399613 1.010964 0.018 Uiso 1 1 calc R . . . .
C19 C 0.5406(2) 0.42088(14) 0.80096(14) 0.0139(4) Uani 1 1 d . . . . .
C20 C 0.6456(2) 0.33738(15) 0.74887(14) 0.0170(4) Uani 1 1 d . . . . .
H20 H 0.738033 0.352071 0.701687 0.020 Uiso 1 1 calc R . . . .
C21 C 0.6122(2) 0.23271(16) 0.76732(16) 0.0224(4) Uani 1 1 d . . . . .
H21 H 0.682719 0.177454 0.732716 0.027 Uiso 1 1 calc R . . . .
C22 C 0.4741(2) 0.21000(16) 0.83710(17) 0.0240(4) Uani 1 1 d . . . . .
H22 H 0.453278 0.139436 0.850436 0.029 Uiso 1 1 calc R . . . .
C23 C 0.3673(2) 0.29285(16) 0.88689(16) 0.0213(4) Uani 1 1 d . . . . .
H23 H 0.273613 0.278127 0.932531 0.026 Uiso 1 1 calc R . . . .
C24 C 0.4000(2) 0.39734(15) 0.86877(15) 0.0169(4) Uani 1 1 d . . . . .
H24 H 0.327510 0.452598 0.902104 0.020 Uiso 1 1 calc R . . . .
C25 C 0.6668(2) 0.85195(15) 0.65806(14) 0.0154(4) Uani 1 1 d . . . . .
H25 H 0.772136 0.848896 0.621823 0.019 Uiso 1 1 calc R . . . .
C26 C 0.5679(2) 0.94962(15) 0.65316(14) 0.0159(4) Uani 1 1 d . . . . .
C27 C 0.4164(2) 0.97082(14) 0.72444(15) 0.0178(4) Uani 1 1 d . . . . .
C28 C 0.6152(2) 1.03734(15) 0.57583(15) 0.0176(4) Uani 1 1 d . . . . .
C29 C 0.7728(3) 0.66653(17) 0.45229(16) 0.0242(4) Uani 1 1 d . . . . .
C30 C 0.7891(3) 0.76441(17) 0.39022(17) 0.0279(5) Uani 1 1 d . . . . .
H30 H 0.716051 0.794484 0.346071 0.033 Uiso 1 1 calc R . . . .
C31 C 0.9108(3) 0.8176(2) 0.39277(18) 0.0376(6) Uani 1 1 d . . . . .
H31 H 0.919405 0.883327 0.350786 0.045 Uiso 1 1 calc R . . . .
C32 C 1.0208(3) 0.7740(2) 0.4574(2) 0.0450(7) Uani 1 1 d . . . . .
H32 H 1.104119 0.809701 0.458801 0.054 Uiso 1 1 calc R . . . .
C33 C 1.0056(3) 0.6758(2) 0.5205(2) 0.0428(7) Uani 1 1 d . . . . .
H33 H 1.079182 0.645630 0.564176 0.051 Uiso 1 1 calc R . . . .
C34 C 0.8814(3) 0.62323(18) 0.51831(17) 0.0314(5) Uani 1 1 d . . . . .
H34 H 0.870878 0.558365 0.561489 0.038 Uiso 1 1 calc R . . . .
C35 C 0.6386(3) 0.6090(2) 0.4465(2) 0.0429(6) Uani 1 1 d . . . . .
H35A H 0.537849 0.655228 0.466887 0.064 Uiso 1 1 calc GR . . . .
H35B H 0.643636 0.543266 0.494571 0.064 Uiso 1 1 calc GR . . . .
H35C H 0.649168 0.591905 0.374484 0.064 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.429(2) . ?
N1 C11 1.466(2) . ?
N1 C12 1.465(3) . ?
N2 C27 1.147(2) . ?
N3 C28 1.145(2) . ?
C1 C2 1.367(3) . ?
C1 C10 1.423(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.400(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(3) . ?
C4 C5 1.442(2) . ?
C4 C13 1.497(2) . ?
C5 C6 1.441(2) . ?
C5 C10 1.434(2) . ?
C6 C7 1.381(2) . ?
C6 C19 1.493(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.401(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.372(2) . ?
C9 C10 1.427(2) . ?
C9 C25 1.474(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.395(2) . ?
C13 C18 1.396(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.398(2) . ?
C19 C24 1.397(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.388(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.386(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.383(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.360(3) . ?
C26 C27 1.435(3) . ?
C26 C28 1.439(3) . ?
C29 C30 1.387(3) . ?
C29 C34 1.383(3) . ?
C29 C35 1.511(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.369(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.380(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.394(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.381(4) . ?
C34 H34 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 115.91(16) . . ?
C1 N1 C12 113.59(15) . . ?
C12 N1 C11 112.10(17) . . ?
C2 C1 N1 124.54(17) . . ?
C2 C1 C10 120.07(17) . . ?
C10 C1 N1 115.40(16) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.88(17) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 118.2 . . ?
C4 C3 C2 123.56(17) . . ?
C4 C3 H3 118.2 . . ?
C3 C4 C5 118.94(16) . . ?
C3 C4 C13 115.28(15) . . ?
C5 C4 C13 125.77(16) . . ?
C6 C5 C4 126.33(16) . . ?
C10 C5 C4 116.75(16) . . ?
C10 C5 C6 116.89(15) . . ?
C5 C6 C19 124.68(15) . . ?
C7 C6 C5 119.37(16) . . ?
C7 C6 C19 115.92(16) . . ?
C6 C7 H7 118.5 . . ?
C6 C7 C8 123.00(17) . . ?
C8 C7 H7 118.5 . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.20(16) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 119.91(16) . . ?
C8 C9 C25 119.90(16) . . ?
C10 C9 C25 119.40(16) . . ?
C1 C10 C5 121.28(16) . . ?
C1 C10 C9 117.70(16) . . ?
C9 C10 C5 120.99(16) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C4 119.29(16) . . ?
C14 C13 C18 118.35(17) . . ?
C18 C13 C4 122.25(16) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.10(17) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.78(18) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.89(18) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.25(17) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.62(17) . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C6 121.56(16) . . ?
C24 C19 C6 119.67(16) . . ?
C24 C19 C20 118.73(17) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.23(17) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.37(18) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.78(18) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.08(18) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 119.6 . . ?
C23 C24 C19 120.77(18) . . ?
C23 C24 H24 119.6 . . ?
C9 C25 H25 117.5 . . ?
C26 C25 C9 124.91(16) . . ?
C26 C25 H25 117.5 . . ?
C25 C26 C27 122.52(16) . . ?
C25 C26 C28 120.10(17) . . ?
C27 C26 C28 117.36(16) . . ?
N2 C27 C26 178.5(2) . . ?
N3 C28 C26 178.8(2) . . ?
C30 C29 C35 119.9(2) . . ?
C34 C29 C30 118.8(2) . . ?
C34 C29 C35 121.3(2) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 C29 121.2(2) . . ?
C31 C30 H30 119.4 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.3(2) . . ?
C32 C31 H31 119.9 . . ?
C31 C32 H32 120.4 . . ?
C31 C32 C33 119.1(2) . . ?
C33 C32 H32 120.4 . . ?
C32 C33 H33 119.9 . . ?
C34 C33 C32 120.2(2) . . ?
C34 C33 H33 119.9 . . ?
C29 C34 H34 119.8 . . ?
C33 C34 C29 120.3(2) . . ?
C33 C34 H34 119.8 . . ?
C29 C35 H35A 109.5 . . ?
C29 C35 H35B 109.5 . . ?
C29 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 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
N1 C1 C2 C3 176.25(17) . . . . ?
N1 C1 C10 C5 -172.63(15) . . . . ?
N1 C1 C10 C9 9.3(2) . . . . ?
C1 C2 C3 C4 -2.9(3) . . . . ?
C2 C1 C10 C5 7.6(3) . . . . ?
C2 C1 C10 C9 -170.55(17) . . . . ?
C2 C3 C4 C5 6.0(3) . . . . ?
C2 C3 C4 C13 -173.38(17) . . . . ?
C3 C4 C5 C6 175.78(17) . . . . ?
C3 C4 C5 C10 -2.3(2) . . . . ?
C3 C4 C13 C14 -57.8(2) . . . . ?
C3 C4 C13 C18 118.33(19) . . . . ?
C4 C5 C6 C7 179.12(17) . . . . ?
C4 C5 C6 C19 -2.7(3) . . . . ?
C4 C5 C10 C1 -4.3(2) . . . . ?
C4 C5 C10 C9 173.76(16) . . . . ?
C4 C13 C14 C15 177.55(17) . . . . ?
C4 C13 C18 C17 -177.18(17) . . . . ?
C5 C4 C13 C14 122.8(2) . . . . ?
C5 C4 C13 C18 -61.0(3) . . . . ?
C5 C6 C7 C8 6.7(3) . . . . ?
C5 C6 C19 C20 -62.3(2) . . . . ?
C5 C6 C19 C24 120.20(19) . . . . ?
C6 C5 C10 C1 177.47(16) . . . . ?
C6 C5 C10 C9 -4.5(2) . . . . ?
C6 C7 C8 C9 -2.9(3) . . . . ?
C6 C19 C20 C21 -179.58(17) . . . . ?
C6 C19 C24 C23 179.65(17) . . . . ?
C7 C6 C19 C20 115.97(19) . . . . ?
C7 C6 C19 C24 -61.5(2) . . . . ?
C7 C8 C9 C10 -4.7(3) . . . . ?
C7 C8 C9 C25 165.09(16) . . . . ?
C8 C9 C10 C1 -173.51(16) . . . . ?
C8 C9 C10 C5 8.4(3) . . . . ?
C8 C9 C25 C26 51.2(3) . . . . ?
C9 C25 C26 C27 14.9(3) . . . . ?
C9 C25 C26 C28 -166.40(17) . . . . ?
C10 C1 C2 C3 -4.0(3) . . . . ?
C10 C5 C6 C7 -2.8(2) . . . . ?
C10 C5 C6 C19 175.36(16) . . . . ?
C10 C9 C25 C26 -139.03(19) . . . . ?
C11 N1 C1 C2 37.0(3) . . . . ?
C11 N1 C1 C10 -142.76(18) . . . . ?
C12 N1 C1 C2 -94.9(2) . . . . ?
C12 N1 C1 C10 85.3(2) . . . . ?
C13 C4 C5 C6 -4.9(3) . . . . ?
C13 C4 C5 C10 177.05(16) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C13 C18 C17 -1.0(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C13 0.1(3) . . . . ?
C18 C13 C14 C15 1.3(3) . . . . ?
C19 C6 C7 C8 -171.66(16) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C19 C24 C23 2.1(3) . . . . ?
C20 C21 C22 C23 1.4(3) . . . . ?
C21 C22 C23 C24 -1.3(3) . . . . ?
C22 C23 C24 C19 -0.4(3) . . . . ?
C24 C19 C20 C21 -2.0(3) . . . . ?
C25 C9 C10 C1 16.7(2) . . . . ?
C25 C9 C10 C5 -161.44(16) . . . . ?
C29 C30 C31 C32 0.3(3) . . . . ?
C30 C29 C34 C33 -1.3(3) . . . . ?
C30 C31 C32 C33 -0.5(3) . . . . ?
C31 C32 C33 C34 -0.2(3) . . . . ?
C32 C33 C34 C29 1.1(3) . . . . ?
C34 C29 C30 C31 0.6(3) . . . . ?
C35 C29 C30 C31 -179.1(2) . . . . ?
C35 C29 C34 C33 178.4(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.082
_oxdiff_exptl_absorpt_empirical_full_min 0.880
_exptl_crystal_recrystallization_method 
'Slow evaporation from a toluene solution'
####################################################################### 
# 
# 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_in063abs100k
_database_code_depnum_ccdc_archive 'CCDC 2016752'
loop_
_audit_author_name
_audit_author_address
'PROFESSOR J D WALLIS'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2020-07-16 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;
_audit_creation_date             2019-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
'2-Cyano-3-(8?-dimethylamino-4?-dimethylammonio-naphthalen-1?-yl)propene-nitrile chloride'
_chemical_formula_moiety         'Cl, H O0.5, C18 H19 N4'
_chemical_formula_sum            'C18 H20 Cl N4 O0.50'
_chemical_formula_weight         335.83
_chemical_absolute_configuration .
_chemical_melting_point          440-443
_chemical_oxdiff_formula         'C18 H18 N4 Cl1'
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'
Cl Cl 0.1484 0.1585 '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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   44.6586(17)
_cell_length_b                   22.6565(7)
_cell_length_c                   6.8837(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6964.9(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    4444
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.9700
_cell_measurement_theta_min      3.7240
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.906
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2832
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-57 -13 0 0.1132
-15 26 5 0.1412
-22 -27 -4 0.1449
56 14 0 0.0262
-29 29 0 0.0470
12 -13 9 0.2004
2 0 -10 0.1946
29 -29 -1 0.0645

_exptl_crystal_recrystallization_method 
'Slow evaporation from a methanol solution.'
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.13
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-57.0321 -13.3175 0.0993 -0.9553 -0.2783 -0.0573
-15.2021 25.5608 4.9843 0.1605 0.0407 -0.9669
-21.8954 -26.8470 -3.9224 -0.6709 -0.2145 0.7028
56.0016 14.3048 -0.0930 0.9601 0.2609 0.0273
-28.8781 28.6383 0.1807 0.1531 -0.4984 -0.8614
12.3263 -13.1809 8.6503 -0.2785 0.9585 -0.0901
1.9716 0.3899 -9.7047 0.2494 -0.8076 0.5373
28.7735 -28.6014 -1.1504 -0.1320 0.4154 0.9132

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       59
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11058
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.272
_diffrn_reflns_theta_min         3.275
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  51.00   1.00   25.00    --  -16.16  57.00 -30.00   84
  2  ω    -83.00   1.00   1.00   25.00    --  -16.16 -57.00 150.00   84
  3  ω    -13.00  88.00   1.00   25.00    --   16.24  19.00 -90.00  101
  4  ω    -33.00  -8.00   1.00   25.00    --  -16.16  57.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0124886000
_diffrn_orient_matrix_UB_12      0.0180821000
_diffrn_orient_matrix_UB_13      -0.0224389000
_diffrn_orient_matrix_UB_21      0.0074585000
_diffrn_orient_matrix_UB_22      -0.0104126000
_diffrn_orient_matrix_UB_23      0.0843094000
_diffrn_orient_matrix_UB_31      0.0063541000
_diffrn_orient_matrix_UB_32      -0.0233229000
_diffrn_orient_matrix_UB_33      -0.0550078000
_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         0.738
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.845
_reflns_number_gt                3763
_reflns_number_total             3948
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1448 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.097
_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)+(0.0355P)²+3.8840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0764
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.22727(2) -0.66721(2) -1.64098(9) 0.01722(13) Uani 1 1 d . . . . .
O1 O -0.250000 -0.750000 -1.3018(5) 0.0352(7) Uani 1 2 d S T P . .
H1 H -0.2419(7) -0.7237(14) -1.384(6) 0.048(10) Uiso 1 1 d . . . . .
N1 N -0.17654(4) -0.59775(8) -1.1686(3) 0.0167(4) Uani 1 1 d . . . . .
N2 N -0.20875(4) -0.34070(8) -1.2863(3) 0.0174(4) Uani 1 1 d . . . . .
H2 H -0.227486 -0.344607 -1.213328 0.021 Uiso 1 1 calc R . . . .
N3 N -0.13406(5) -0.69928(8) -1.6581(4) 0.0258(5) Uani 1 1 d . . . . .
N4 N -0.09605(5) -0.53240(9) -1.4743(4) 0.0257(5) Uani 1 1 d . . . . .
C1 C -0.19471(5) -0.54802(9) -1.0978(4) 0.0145(5) Uani 1 1 d . . . . .
C2 C -0.21021(5) -0.54369(10) -0.9289(4) 0.0182(5) Uani 1 1 d . . . . .
H2A H -0.211970 -0.575459 -0.844144 0.022 Uiso 1 1 calc R . . . .
C3 C -0.22358(5) -0.48826(10) -0.8881(4) 0.0195(5) Uani 1 1 d . . . . .
H3 H -0.235003 -0.484322 -0.775907 0.023 Uiso 1 1 calc R . . . .
C4 C -0.22034(5) -0.44023(10) -1.0078(4) 0.0179(5) Uani 1 1 d . . . . .
H4 H -0.228723 -0.404221 -0.972468 0.021 Uiso 1 1 calc R . . . .
C5 C -0.20432(5) -0.44511(9) -1.1847(3) 0.0134(5) Uani 1 1 d . . . . .
C6 C -0.19839(5) -0.40128(9) -1.3277(4) 0.0150(5) Uani 1 1 d . . . . .
C7 C -0.18239(5) -0.41365(10) -1.4917(4) 0.0169(5) Uani 1 1 d . . . . .
H7 H -0.178513 -0.383389 -1.579463 0.020 Uiso 1 1 calc R . . . .
C8 C -0.17148(5) -0.47118(10) -1.5327(4) 0.0156(5) Uani 1 1 d . . . . .
H8 H -0.160932 -0.478839 -1.646474 0.019 Uiso 1 1 calc R . . . .
C9 C -0.17685(5) -0.51498(9) -1.4009(4) 0.0130(4) Uani 1 1 d . . . . .
C10 C -0.19231(5) -0.50117(9) -1.2287(4) 0.0131(4) Uani 1 1 d . . . . .
C11 C -0.14742(6) -0.59871(12) -1.0644(4) 0.0253(6) Uani 1 1 d . . . . .
H11A H -0.137903 -0.560881 -1.076252 0.038 Uiso 1 1 calc GR . . . .
H11B H -0.134759 -0.628507 -1.119919 0.038 Uiso 1 1 calc GR . . . .
H11C H -0.150767 -0.607346 -0.929583 0.038 Uiso 1 1 calc GR . . . .
C12 C -0.19199(6) -0.65583(9) -1.1527(5) 0.0275(6) Uani 1 1 d . . . . .
H12A H -0.195164 -0.665137 -1.018230 0.041 Uiso 1 1 calc GR . . . .
H12B H -0.179815 -0.685877 -1.211334 0.041 Uiso 1 1 calc GR . . . .
H12C H -0.210929 -0.653911 -1.218327 0.041 Uiso 1 1 calc GR . . . .
C13 C -0.18726(6) -0.30884(11) -1.1556(6) 0.0353(8) Uani 1 1 d . . . . .
H13A H -0.183080 -0.332788 -1.043764 0.053 Uiso 1 1 calc GR . . . .
H13B H -0.195967 -0.272143 -1.114717 0.053 Uiso 1 1 calc GR . . . .
H13C H -0.168989 -0.301213 -1.224618 0.053 Uiso 1 1 calc GR . . . .
C14 C -0.21589(6) -0.30473(11) -1.4623(5) 0.0322(7) Uani 1 1 d . . . . .
H14A H -0.197817 -0.296962 -1.533358 0.048 Uiso 1 1 calc GR . . . .
H14B H -0.224825 -0.268066 -1.423276 0.048 Uiso 1 1 calc GR . . . .
H14C H -0.229624 -0.326077 -1.543442 0.048 Uiso 1 1 calc GR . . . .
C15 C -0.17045(5) -0.58007(9) -1.4128(4) 0.0155(5) Uani 1 1 d . . . . .
H15 H -0.1871(5) -0.5998(11) -1.469(4) 0.011(6) Uiso 1 1 d . . . . .
C16 C -0.14245(5) -0.59893(10) -1.4928(4) 0.0162(5) Uani 1 1 d . . . . .
C17 C -0.13846(5) -0.65497(10) -1.5823(4) 0.0185(5) Uani 1 1 d . . . . .
C18 C -0.11687(5) -0.56212(10) -1.4818(4) 0.0176(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
N1 C1 1.471(3) . ?
N1 C11 1.486(3) . ?
N1 C12 1.490(3) . ?
N1 C15 1.749(3) . ?
N2 C6 1.476(3) . ?
N2 C13 1.500(4) . ?
N2 C14 1.495(3) . ?
N3 C17 1.149(3) . ?
N4 C18 1.149(3) . ?
C1 C2 1.357(3) . ?
C1 C10 1.396(3) . ?
C2 C3 1.419(3) . ?
C3 C4 1.372(3) . ?
C4 C5 1.417(3) . ?
C5 C6 1.423(3) . ?
C5 C10 1.411(3) . ?
C6 C7 1.365(4) . ?
C7 C8 1.420(3) . ?
C8 C9 1.366(3) . ?
C9 C10 1.407(3) . ?
C9 C15 1.504(3) . ?
C15 C16 1.431(3) . ?
C16 C17 1.423(3) . ?
C16 C18 1.416(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 109.50(19) . . ?
C1 N1 C12 113.38(18) . . ?
C1 N1 C15 103.21(16) . . ?
C11 N1 C12 110.9(2) . . ?
C11 N1 C15 109.35(17) . . ?
C12 N1 C15 110.17(19) . . ?
C6 N2 C13 111.28(18) . . ?
C6 N2 C14 114.6(2) . . ?
C14 N2 C13 111.1(2) . . ?
C2 C1 N1 128.3(2) . . ?
C2 C1 C10 122.5(2) . . ?
C10 C1 N1 109.0(2) . . ?
C1 C2 C3 116.6(2) . . ?
C4 C3 C2 122.6(2) . . ?
C3 C4 C5 120.5(2) . . ?
C4 C5 C6 129.3(2) . . ?
C10 C5 C4 116.5(2) . . ?
C10 C5 C6 114.1(2) . . ?
C5 C6 N2 117.2(2) . . ?
C7 C6 N2 121.0(2) . . ?
C7 C6 C5 121.7(2) . . ?
C6 C7 C8 122.2(2) . . ?
C9 C8 C7 118.3(2) . . ?
C8 C9 C10 118.97(19) . . ?
C8 C9 C15 130.0(2) . . ?
C10 C9 C15 110.93(19) . . ?
C1 C10 C5 121.1(2) . . ?
C1 C10 C9 114.3(2) . . ?
C9 C10 C5 124.6(2) . . ?
C9 C15 N1 98.19(18) . . ?
C16 C15 N1 115.90(19) . . ?
C16 C15 C9 118.65(19) . . ?
C17 C16 C15 122.8(2) . . ?
C18 C16 C15 120.6(2) . . ?
C18 C16 C17 116.6(2) . . ?
N3 C17 C16 176.9(3) . . ?
N4 C18 C16 179.5(3) . . ?

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
N1 C1 C2 C3 174.1(2) . . . . ?
N1 C1 C10 C5 -171.74(19) . . . . ?
N1 C1 C10 C9 7.4(3) . . . . ?
N1 C15 C16 C17 89.6(3) . . . . ?
N1 C15 C16 C18 -89.0(3) . . . . ?
N2 C6 C7 C8 178.3(2) . . . . ?
C1 N1 C15 C9 19.92(19) . . . . ?
C1 N1 C15 C16 147.38(19) . . . . ?
C1 C2 C3 C4 -2.4(4) . . . . ?
C2 C1 C10 C5 4.4(3) . . . . ?
C2 C1 C10 C9 -176.5(2) . . . . ?
C2 C3 C4 C5 3.0(4) . . . . ?
C3 C4 C5 C6 -179.9(2) . . . . ?
C3 C4 C5 C10 0.1(3) . . . . ?
C4 C5 C6 N2 3.5(4) . . . . ?
C4 C5 C6 C7 -180.0(2) . . . . ?
C4 C5 C10 C1 -3.7(3) . . . . ?
C4 C5 C10 C9 177.3(2) . . . . ?
C5 C6 C7 C8 2.0(3) . . . . ?
C6 C5 C10 C1 176.3(2) . . . . ?
C6 C5 C10 C9 -2.7(3) . . . . ?
C6 C7 C8 C9 -1.2(3) . . . . ?
C7 C8 C9 C10 -1.4(3) . . . . ?
C7 C8 C9 C15 174.2(2) . . . . ?
C8 C9 C10 C1 -175.6(2) . . . . ?
C8 C9 C10 C5 3.5(3) . . . . ?
C8 C9 C15 N1 167.5(2) . . . . ?
C8 C9 C15 C16 42.0(4) . . . . ?
C9 C15 C16 C17 -154.0(2) . . . . ?
C9 C15 C16 C18 27.4(4) . . . . ?
C10 C1 C2 C3 -1.3(3) . . . . ?
C10 C5 C6 N2 -176.53(19) . . . . ?
C10 C5 C6 C7 -0.1(3) . . . . ?
C10 C9 C15 N1 -16.6(2) . . . . ?
C10 C9 C15 C16 -142.2(2) . . . . ?
C11 N1 C1 C2 -76.4(3) . . . . ?
C11 N1 C1 C10 99.5(2) . . . . ?
C11 N1 C15 C9 -96.57(19) . . . . ?
C11 N1 C15 C16 30.9(3) . . . . ?
C12 N1 C1 C2 48.0(3) . . . . ?
C12 N1 C1 C10 -136.1(2) . . . . ?
C12 N1 C15 C9 141.28(18) . . . . ?
C12 N1 C15 C16 -91.3(2) . . . . ?
C13 N2 C6 C5 81.2(3) . . . . ?
C13 N2 C6 C7 -95.2(3) . . . . ?
C14 N2 C6 C5 -151.6(2) . . . . ?
C14 N2 C6 C7 31.9(3) . . . . ?
C15 N1 C1 C2 167.2(2) . . . . ?
C15 N1 C1 C10 -16.9(2) . . . . ?
C15 C9 C10 C1 8.1(3) . . . . ?
C15 C9 C10 C5 -172.9(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.072
_oxdiff_exptl_absorpt_empirical_full_min 0.917
####################################################################### 
# 
# 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_400JW260
_database_code_depnum_ccdc_archive 'CCDC 2016753'
loop_
_audit_author_name
_audit_author_address
'PROFESSOR J D WALLIS'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2020-07-16 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'Methyl E-2-cyano-3-(8?-dimethylamino-4?-dimethylammonio-naphthalen-1?-yl)-2-propenoate chloride'
_chemical_name_common            ?
_chemical_melting_point          397-400
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 Cl N3 O2.50'
_chemical_formula_weight         368.85

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   48.4820(18)
_cell_length_b                   22.8029(9)
_cell_length_c                   6.7460(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7457.9(5)
_cell_formula_units_Z            16
_cell_measurement_temperature    260(2)
_cell_measurement_reflns_used    3784
_cell_measurement_theta_min      3.6700
_cell_measurement_theta_max      22.3370

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             3120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.083
_exptl_absorpt_coefficient_mu    0.225
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.97473
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      260.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            11484
_diffrn_reflns_av_unetI/netI     0.0851
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_limit_h_min       -64
_diffrn_reflns_limit_h_max       61
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.362
_diffrn_reflns_theta_max         28.261
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             4286
_reflns_number_gt                2977
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_max     0.885
_reflns_Friedel_fraction_full    0.934

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0308P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 954 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4286
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.50822(2) 0.38414(5) 0.6455(2) 0.0510(4) Uani 1 1 d . . . . .
O1 O 0.41770(6) 0.51072(12) 0.8208(5) 0.0433(8) Uani 1 1 d . . . . .
O2 O 0.37235(5) 0.48927(12) 0.8317(5) 0.0435(8) Uani 1 1 d . . . . .
O3 O 0.5000 0.5000 0.9238(10) 0.0772(18) Uani 1 2 d S T P . .
N1 N 0.44021(6) 0.42910(13) 0.3910(5) 0.0312(8) Uani 1 1 d . . . . .
N2 N 0.44891(7) 0.16403(14) 0.4173(7) 0.0370(9) Uani 1 1 d . . . . .
H20 H 0.4656(8) 0.1591(16) 0.336(7) 0.044 Uiso 1 1 d . U . . .
N3 N 0.35894(7) 0.36213(16) 0.6027(7) 0.0559(12) Uani 1 1 d . . . . .
C1 C 0.45258(8) 0.37642(16) 0.3008(6) 0.0285(9) Uani 1 1 d . . . . .
C2 C 0.46588(8) 0.37244(17) 0.1256(7) 0.0370(10) Uani 1 1 d . . . . .
H2 H 0.4693 0.4054 0.0481 0.044 Uiso 1 1 calc R U . . .
C3 C 0.47442(8) 0.31572(18) 0.0651(7) 0.0397(11) Uani 1 1 d . . . . .
H3 H 0.4841 0.3118 -0.0532 0.048 Uiso 1 1 calc R U . . .
C4 C 0.46893(7) 0.26661(18) 0.1745(7) 0.0360(10) Uani 1 1 d . . . . .
H4 H 0.4746 0.2301 0.1283 0.043 Uiso 1 1 calc R U . . .
C5 C 0.45481(7) 0.27078(17) 0.3568(6) 0.0276(9) Uani 1 1 d . . . . .
C6 C 0.44579(7) 0.22505(17) 0.4846(6) 0.0309(10) Uani 1 1 d . . . . .
C7 C 0.43165(8) 0.23666(18) 0.6541(7) 0.0394(11) Uani 1 1 d . . . . .
H7 H 0.4261 0.2057 0.7346 0.047 Uiso 1 1 calc R U . . .
C8 C 0.42521(8) 0.29490(18) 0.7109(7) 0.0368(11) Uani 1 1 d . . . . .
H8 H 0.4157 0.3023 0.8279 0.044 Uiso 1 1 calc R U . . .
C9 C 0.43318(7) 0.33953(17) 0.5922(6) 0.0288(9) Uani 1 1 d . . . . .
C10 C 0.44739(7) 0.32745(16) 0.4173(6) 0.0249(8) Uani 1 1 d . . . . .
C11 C 0.41622(8) 0.4495(2) 0.2725(7) 0.0456(12) Uani 1 1 d . . . . .
H11C H 0.4222 0.4595 0.1411 0.068 Uiso 1 1 calc R U . . .
H11A H 0.4082 0.4834 0.3344 0.068 Uiso 1 1 calc R U . . .
H11B H 0.4027 0.4188 0.2653 0.068 Uiso 1 1 calc R U . . .
C12 C 0.46008(8) 0.47801(17) 0.4164(8) 0.0452(12) Uani 1 1 d . . . . .
H12A H 0.4759 0.4643 0.4883 0.068 Uiso 1 1 calc R U . . .
H12C H 0.4514 0.5093 0.4886 0.068 Uiso 1 1 calc R U . . .
H12B H 0.4658 0.4921 0.2886 0.068 Uiso 1 1 calc R U . . .
C13 C 0.42881(8) 0.40380(18) 0.6226(7) 0.0325(10) Uani 1 1 d . . . . .
H13 H 0.4414(7) 0.4220(17) 0.693(7) 0.037(12) Uiso 1 1 d . . . . .
C14 C 0.40162(7) 0.42299(17) 0.6803(7) 0.0319(10) Uani 1 1 d . . . . .
C15 C 0.39906(8) 0.47710(19) 0.7799(6) 0.0339(10) Uani 1 1 d . . . . .
C16 C 0.37814(8) 0.38916(18) 0.6369(8) 0.0375(10) Uani 1 1 d . . . . .
C17 C 0.36805(9) 0.5432(2) 0.9355(8) 0.0576(15) Uani 1 1 d . . . . .
H17C H 0.3709 0.5755 0.8467 0.086 Uiso 1 1 calc R U . . .
H17A H 0.3808 0.5459 1.0439 0.086 Uiso 1 1 calc R U . . .
H17B H 0.3495 0.5444 0.9856 0.086 Uiso 1 1 calc R U . . .
C18 C 0.42513(9) 0.1483(2) 0.2851(9) 0.0602(16) Uani 1 1 d . . . . .
H18A H 0.4083 0.1498 0.3597 0.090 Uiso 1 1 calc R U . . .
H18B H 0.4277 0.1094 0.2339 0.090 Uiso 1 1 calc R U . . .
H18C H 0.4242 0.1756 0.1770 0.090 Uiso 1 1 calc R U . . .
H30 H 0.5026(14) 0.470(2) 0.849(12) 0.13(3) Uiso 1 1 d . . . . .
C19 C 0.45276(10) 0.12001(18) 0.5808(8) 0.0555(15) Uani 1 1 d . . . . .
H19A H 0.4673 0.1328 0.6669 0.083 Uiso 1 1 calc R U . . .
H19C H 0.4574 0.0826 0.5248 0.083 Uiso 1 1 calc R U . . .
H19B H 0.4360 0.1166 0.6553 0.083 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
O1 C15 1.217(5) . ?
O2 C15 1.369(5) . ?
O2 C17 1.430(5) . ?
O3 H30 0.87(6) . ?
N1 C1 1.474(5) . ?
N1 C12 1.484(4) . ?
N1 C11 1.487(5) . ?
N1 C13 1.754(6) . ?
N2 C6 1.471(5) . ?
N2 C18 1.501(6) . ?
N2 C19 1.503(6) . ?
N2 H20 0.98(4) . ?
N3 C16 1.140(5) . ?
C1 C2 1.350(6) . ?
C1 C10 1.388(5) . ?
C2 C3 1.418(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.410(6) . ?
C4 H4 0.9300 . ?
C5 C10 1.402(5) . ?
C5 C6 1.422(5) . ?
C6 C7 1.360(6) . ?
C7 C8 1.417(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.351(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(6) . ?
C9 C13 1.495(6) . ?
C11 H11C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12C 0.9600 . ?
C12 H12B 0.9600 . ?
C13 C14 1.442(5) . ?
C13 H13 0.88(4) . ?
C14 C16 1.406(5) . ?
C14 C15 1.411(5) . ?
C17 H17C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19B 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
C15 O2 C17 115.9(3) . . ?
C1 N1 C12 113.3(3) . . ?
C1 N1 C11 110.6(3) . . ?
C12 N1 C11 109.6(3) . . ?
C1 N1 C13 103.2(3) . . ?
C12 N1 C13 110.4(3) . . ?
C11 N1 C13 109.6(3) . . ?
C6 N2 C18 109.3(3) . . ?
C6 N2 C19 114.7(4) . . ?
C18 N2 C19 111.8(3) . . ?
C6 N2 H20 111(2) . . ?
C18 N2 H20 106(3) . . ?
C19 N2 H20 103(2) . . ?
C2 C1 C10 121.9(4) . . ?
C2 C1 N1 127.6(4) . . ?
C10 C1 N1 110.4(4) . . ?
C1 C2 C3 116.9(4) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C4 C3 C2 122.3(4) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 120.7(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C10 C5 C4 116.1(4) . . ?
C10 C5 C6 114.9(4) . . ?
C4 C5 C6 128.9(4) . . ?
C7 C6 C5 121.5(4) . . ?
C7 C6 N2 119.7(4) . . ?
C5 C6 N2 118.3(4) . . ?
C6 C7 C8 121.4(4) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 118.9(4) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 119.6(4) . . ?
C8 C9 C13 128.1(4) . . ?
C10 C9 C13 112.3(4) . . ?
C1 C10 C9 114.2(4) . . ?
C1 C10 C5 122.0(4) . . ?
C9 C10 C5 123.7(4) . . ?
N1 C11 H11C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
H11C C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11C C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
C14 C13 C9 117.6(3) . . ?
C14 C13 N1 115.4(3) . . ?
C9 C13 N1 99.0(3) . . ?
C14 C13 H13 110(3) . . ?
C9 C13 H13 116(3) . . ?
N1 C13 H13 96(3) . . ?
C16 C14 C15 120.5(3) . . ?
C16 C14 C13 121.2(4) . . ?
C15 C14 C13 118.3(3) . . ?
O1 C15 O2 121.1(4) . . ?
O1 C15 C14 126.4(4) . . ?
O2 C15 C14 112.5(4) . . ?
N3 C16 C14 179.3(5) . . ?
O2 C17 H17C 109.5 . . ?
O2 C17 H17A 109.5 . . ?
H17C C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17C C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19C C19 H19B 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
C12 N1 C1 C2 -56.6(5) . . . . ?
C11 N1 C1 C2 66.9(5) . . . . ?
C13 N1 C1 C2 -176.0(4) . . . . ?
C12 N1 C1 C10 127.1(4) . . . . ?
C11 N1 C1 C10 -109.4(4) . . . . ?
C13 N1 C1 C10 7.7(4) . . . . ?
C10 C1 C2 C3 -0.1(6) . . . . ?
N1 C1 C2 C3 -176.0(4) . . . . ?
C1 C2 C3 C4 1.8(6) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
C3 C4 C5 C10 -0.9(6) . . . . ?
C3 C4 C5 C6 175.8(4) . . . . ?
C10 C5 C6 C7 -1.5(6) . . . . ?
C4 C5 C6 C7 -178.2(4) . . . . ?
C10 C5 C6 N2 170.7(3) . . . . ?
C4 C5 C6 N2 -6.0(6) . . . . ?
C18 N2 C6 C7 89.7(5) . . . . ?
C19 N2 C6 C7 -36.8(5) . . . . ?
C18 N2 C6 C5 -82.7(4) . . . . ?
C19 N2 C6 C5 150.8(4) . . . . ?
C5 C6 C7 C8 0.1(6) . . . . ?
N2 C6 C7 C8 -172.0(4) . . . . ?
C6 C7 C8 C9 0.6(6) . . . . ?
C7 C8 C9 C10 0.2(6) . . . . ?
C7 C8 C9 C13 -179.7(4) . . . . ?
C2 C1 C10 C9 -179.3(4) . . . . ?
N1 C1 C10 C9 -2.7(4) . . . . ?
C2 C1 C10 C5 -2.2(6) . . . . ?
N1 C1 C10 C5 174.4(3) . . . . ?
C8 C9 C10 C1 175.3(4) . . . . ?
C13 C9 C10 C1 -4.8(5) . . . . ?
C8 C9 C10 C5 -1.7(6) . . . . ?
C13 C9 C10 C5 178.1(3) . . . . ?
C4 C5 C10 C1 2.6(5) . . . . ?
C6 C5 C10 C1 -174.5(3) . . . . ?
C4 C5 C10 C9 179.5(4) . . . . ?
C6 C5 C10 C9 2.3(5) . . . . ?
C8 C9 C13 C14 -46.6(6) . . . . ?
C10 C9 C13 C14 133.5(4) . . . . ?
C8 C9 C13 N1 -171.6(4) . . . . ?
C10 C9 C13 N1 8.6(4) . . . . ?
C1 N1 C13 C14 -136.0(3) . . . . ?
C12 N1 C13 C14 102.6(4) . . . . ?
C11 N1 C13 C14 -18.2(4) . . . . ?
C1 N1 C13 C9 -9.5(3) . . . . ?
C12 N1 C13 C9 -130.9(3) . . . . ?
C11 N1 C13 C9 108.3(3) . . . . ?
C9 C13 C14 C16 -24.2(6) . . . . ?
N1 C13 C14 C16 92.1(5) . . . . ?
C9 C13 C14 C15 156.5(4) . . . . ?
N1 C13 C14 C15 -87.2(5) . . . . ?
C17 O2 C15 O1 -0.1(6) . . . . ?
C17 O2 C15 C14 179.3(4) . . . . ?
C16 C14 C15 O1 -178.0(5) . . . . ?
C13 C14 C15 O1 1.3(7) . . . . ?
C16 C14 C15 O2 2.6(6) . . . . ?
C13 C14 C15 O2 -178.1(4) . . . . ?

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
N2 H20 Cl1 0.98(4) 2.06(4) 2.981(4) 155(3) 6_654
O3 H30 Cl1 0.87(6) 2.40(6) 3.265(4) 178(7) .

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.048

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Slow evaporation from an acetonitrile solution'
####################################################################### 
# 
# 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_JB400AB150
_database_code_depnum_ccdc_archive 'CCDC 2016754'
loop_
_audit_author_name
_audit_author_address
'PROFESSOR J D WALLIS'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2020-07-16 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'Methyl E-2-cyano-3-(8?-dimethylamino-4?-dimethylammonio-naphthalen-1?-yl)-2-prop-enoate chloride'
_chemical_name_common            ?
_chemical_melting_point          397-400
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 Cl N3 O2.50'
_chemical_formula_weight         368.85

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   48.2476(11)
_cell_length_b                   22.8006(6)
_cell_length_c                   6.6691(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7336.5(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8710
_cell_measurement_theta_min      3.8130
_cell_measurement_theta_max      30.0350

_exptl_crystal_description       block
_exptl_crystal_colour            orange

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             3120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.083
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            27475
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -64
_diffrn_reflns_limit_h_max       63
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.210
_diffrn_reflns_theta_max         28.275
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4465
_reflns_number_gt                4051
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    0.963

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0349P)²+4.4995P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1685 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4465
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0780
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.50878(2) 0.38505(3) 0.64154(9) 0.02692(15) Uani 1 1 d . . . . .
O1 O 0.41821(3) 0.51292(7) 0.8214(3) 0.0241(4) Uani 1 1 d . . . . .
O2 O 0.37254(3) 0.49107(7) 0.8351(3) 0.0249(4) Uani 1 1 d . . . . .
O3 O 0.5000 0.5000 0.9268(5) 0.0405(7) Uani 1 2 d S T P . .
N1 N 0.44041(4) 0.42960(8) 0.3945(3) 0.0171(4) Uani 1 1 d . . . . .
N2 N 0.44863(4) 0.16456(8) 0.4188(3) 0.0200(4) Uani 1 1 d . . . . .
H20 H 0.4642(5) 0.1586(11) 0.341(4) 0.024 Uiso 1 1 d . U . . .
N3 N 0.35896(4) 0.36230(10) 0.6096(4) 0.0315(5) Uani 1 1 d . . . . .
C1 C 0.45313(5) 0.37732(9) 0.3021(3) 0.0168(4) Uani 1 1 d . . . . .
C2 C 0.46680(5) 0.37347(10) 0.1247(4) 0.0213(5) Uani 1 1 d . . . . .
H2 H 0.4706 0.4072 0.0456 0.026 Uiso 1 1 calc R U . . .
C3 C 0.47524(5) 0.31642(11) 0.0630(4) 0.0237(5) Uani 1 1 d . . . . .
H3 H 0.4851 0.3125 -0.0594 0.028 Uiso 1 1 calc R U . . .
C4 C 0.46968(5) 0.26687(10) 0.1725(4) 0.0207(5) Uani 1 1 d . . . . .
H4 H 0.4755 0.2296 0.1245 0.025 Uiso 1 1 calc R U . . .
C5 C 0.45525(4) 0.27125(9) 0.3577(3) 0.0165(4) Uani 1 1 d . . . . .
C6 C 0.44597(4) 0.22565(10) 0.4870(3) 0.0177(5) Uani 1 1 d . . . . .
C7 C 0.43168(5) 0.23748(10) 0.6591(4) 0.0218(5) Uani 1 1 d . . . . .
H7 H 0.4258 0.2059 0.7416 0.026 Uiso 1 1 calc R U . . .
C8 C 0.42544(5) 0.29560(10) 0.7174(4) 0.0213(5) Uani 1 1 d . . . . .
H8 H 0.4157 0.3032 0.8386 0.026 Uiso 1 1 calc R U . . .
C9 C 0.43361(4) 0.34049(10) 0.5966(3) 0.0168(4) Uani 1 1 d . . . . .
C10 C 0.44785(4) 0.32808(9) 0.4194(3) 0.0158(4) Uani 1 1 d . . . . .
C11 C 0.41637(5) 0.44972(11) 0.2723(4) 0.0253(5) Uani 1 1 d . . . . .
H11C H 0.4228 0.4608 0.1382 0.038 Uiso 1 1 calc R U . . .
H11A H 0.4077 0.4836 0.3372 0.038 Uiso 1 1 calc R U . . .
H11B H 0.4028 0.4179 0.2612 0.038 Uiso 1 1 calc R U . . .
C12 C 0.46041(5) 0.47937(10) 0.4194(4) 0.0237(5) Uani 1 1 d . . . . .
H12A H 0.4768 0.4657 0.4922 0.036 Uiso 1 1 calc R U . . .
H12C H 0.4515 0.5111 0.4951 0.036 Uiso 1 1 calc R U . . .
H12B H 0.4660 0.4939 0.2871 0.036 Uiso 1 1 calc R U . . .
C13 C 0.42950(5) 0.40521(10) 0.6229(3) 0.0173(4) Uani 1 1 d . . . . .
H13 H 0.4431(5) 0.4232(11) 0.696(4) 0.012(6) Uiso 1 1 d . . . . .
C14 C 0.40202(4) 0.42450(10) 0.6822(4) 0.0188(5) Uani 1 1 d . . . . .
C15 C 0.39933(5) 0.47922(10) 0.7814(3) 0.0191(5) Uani 1 1 d . . . . .
C16 C 0.37836(4) 0.39035(10) 0.6416(4) 0.0210(5) Uani 1 1 d . . . . .
C17 C 0.36853(5) 0.54583(12) 0.9361(4) 0.0333(6) Uani 1 1 d . . . . .
H17C H 0.3723 0.5782 0.8431 0.050 Uiso 1 1 calc R U . . .
H17A H 0.3812 0.5484 1.0505 0.050 Uiso 1 1 calc R U . . .
H17B H 0.3494 0.5484 0.9839 0.050 Uiso 1 1 calc R U . . .
C18 C 0.42467(5) 0.14967(12) 0.2836(5) 0.0318(6) Uani 1 1 d . . . . .
H18A H 0.4073 0.1523 0.3594 0.048 Uiso 1 1 calc R U . . .
H18B H 0.4269 0.1097 0.2323 0.048 Uiso 1 1 calc R U . . .
H18C H 0.4242 0.1773 0.1711 0.048 Uiso 1 1 calc R U . . .
H30 H 0.5023(8) 0.4720(15) 0.848(7) 0.067(13) Uiso 1 1 d . . . . .
C19 C 0.45193(6) 0.11986(11) 0.5824(4) 0.0292(6) Uani 1 1 d . . . . .
H19A H 0.4670 0.1318 0.6722 0.044 Uiso 1 1 calc R U . . .
H19C H 0.4563 0.0817 0.5231 0.044 Uiso 1 1 calc R U . . .
H19B H 0.4346 0.1169 0.6586 0.044 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
O1 C15 1.221(3) . ?
O2 C15 1.368(3) . ?
O2 C17 1.432(3) . ?
O3 H30 0.84(4) . ?
N1 C1 1.476(3) . ?
N1 C11 1.490(3) . ?
N1 C12 1.499(3) . ?
N1 C13 1.705(3) . ?
N2 C6 1.471(3) . ?
N2 C19 1.501(3) . ?
N2 C18 1.505(3) . ?
N2 H20 0.92(3) . ?
N3 C16 1.154(3) . ?
C1 C2 1.358(3) . ?
C1 C10 1.392(3) . ?
C2 C3 1.424(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.421(3) . ?
C4 H4 0.9500 . ?
C5 C10 1.406(3) . ?
C5 C6 1.423(3) . ?
C6 C7 1.366(3) . ?
C7 C8 1.414(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.361(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(3) . ?
C9 C13 1.499(3) . ?
C11 H11C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12C 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C14 1.452(3) . ?
C13 H13 0.92(2) . ?
C14 C16 1.408(3) . ?
C14 C15 1.418(3) . ?
C17 H17C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19C 0.9800 . ?
C19 H19B 0.9800 . ?

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
C15 O2 C17 115.04(18) . . ?
C1 N1 C11 110.12(18) . . ?
C1 N1 C12 112.96(17) . . ?
C11 N1 C12 109.19(18) . . ?
C1 N1 C13 103.77(16) . . ?
C11 N1 C13 110.41(16) . . ?
C12 N1 C13 110.30(17) . . ?
C6 N2 C19 115.3(2) . . ?
C6 N2 C18 109.38(18) . . ?
C19 N2 C18 111.32(19) . . ?
C6 N2 H20 112.6(17) . . ?
C19 N2 H20 103.0(17) . . ?
C18 N2 H20 104.7(17) . . ?
C2 C1 C10 121.8(2) . . ?
C2 C1 N1 128.2(2) . . ?
C10 C1 N1 109.9(2) . . ?
C1 C2 C3 116.7(2) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C4 C3 C2 122.9(2) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C10 C5 C4 116.3(2) . . ?
C10 C5 C6 114.6(2) . . ?
C4 C5 C6 129.0(2) . . ?
C7 C6 C5 121.6(2) . . ?
C7 C6 N2 119.4(2) . . ?
C5 C6 N2 118.5(2) . . ?
C6 C7 C8 121.6(2) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C7 118.7(2) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 119.4(2) . . ?
C8 C9 C13 129.2(2) . . ?
C10 C9 C13 111.33(19) . . ?
C1 C10 C9 113.7(2) . . ?
C1 C10 C5 122.2(2) . . ?
C9 C10 C5 124.0(2) . . ?
N1 C11 H11C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
H11C C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11C C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
C14 C13 C9 116.81(19) . . ?
C14 C13 N1 115.23(18) . . ?
C9 C13 N1 100.12(16) . . ?
C14 C13 H13 111.9(15) . . ?
C9 C13 H13 114.2(15) . . ?
N1 C13 H13 96.3(15) . . ?
C16 C14 C15 120.1(2) . . ?
C16 C14 C13 121.4(2) . . ?
C15 C14 C13 118.5(2) . . ?
O1 C15 O2 121.5(2) . . ?
O1 C15 C14 126.0(2) . . ?
O2 C15 C14 112.48(19) . . ?
N3 C16 C14 179.6(3) . . ?
O2 C17 H17C 109.5 . . ?
O2 C17 H17A 109.5 . . ?
H17C C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17C C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19C C19 H19B 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
C11 N1 C1 C2 66.7(3) . . . . ?
C12 N1 C1 C2 -55.6(3) . . . . ?
C13 N1 C1 C2 -175.1(2) . . . . ?
C11 N1 C1 C10 -109.6(2) . . . . ?
C12 N1 C1 C10 128.1(2) . . . . ?
C13 N1 C1 C10 8.6(2) . . . . ?
C10 C1 C2 C3 0.7(3) . . . . ?
N1 C1 C2 C3 -175.3(2) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C10 -1.1(3) . . . . ?
C3 C4 C5 C6 175.7(2) . . . . ?
C10 C5 C6 C7 -1.6(3) . . . . ?
C4 C5 C6 C7 -178.4(2) . . . . ?
C10 C5 C6 N2 170.02(18) . . . . ?
C4 C5 C6 N2 -6.8(3) . . . . ?
C19 N2 C6 C7 -36.5(3) . . . . ?
C18 N2 C6 C7 89.8(3) . . . . ?
C19 N2 C6 C5 151.6(2) . . . . ?
C18 N2 C6 C5 -82.0(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
N2 C6 C7 C8 -171.7(2) . . . . ?
C6 C7 C8 C9 1.0(4) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C7 C8 C9 C13 179.6(2) . . . . ?
C2 C1 C10 C9 179.9(2) . . . . ?
N1 C1 C10 C9 -3.5(3) . . . . ?
C2 C1 C10 C5 -2.7(3) . . . . ?
N1 C1 C10 C5 173.85(18) . . . . ?
C8 C9 C10 C1 175.3(2) . . . . ?
C13 C9 C10 C1 -4.3(3) . . . . ?
C8 C9 C10 C5 -2.0(3) . . . . ?
C13 C9 C10 C5 178.38(19) . . . . ?
C4 C5 C10 C1 2.9(3) . . . . ?
C6 C5 C10 C1 -174.4(2) . . . . ?
C4 C5 C10 C9 179.9(2) . . . . ?
C6 C5 C10 C9 2.7(3) . . . . ?
C8 C9 C13 C14 -45.7(3) . . . . ?
C10 C9 C13 C14 134.0(2) . . . . ?
C8 C9 C13 N1 -170.8(2) . . . . ?
C10 C9 C13 N1 8.8(2) . . . . ?
C1 N1 C13 C14 -136.46(19) . . . . ?
C11 N1 C13 C14 -18.5(2) . . . . ?
C12 N1 C13 C14 102.3(2) . . . . ?
C1 N1 C13 C9 -10.26(19) . . . . ?
C11 N1 C13 C9 107.71(19) . . . . ?
C12 N1 C13 C9 -131.52(17) . . . . ?
C9 C13 C14 C16 -24.4(3) . . . . ?
N1 C13 C14 C16 92.8(3) . . . . ?
C9 C13 C14 C15 156.1(2) . . . . ?
N1 C13 C14 C15 -86.7(3) . . . . ?
C17 O2 C15 O1 1.3(3) . . . . ?
C17 O2 C15 C14 180.0(2) . . . . ?
C16 C14 C15 O1 -178.7(2) . . . . ?
C13 C14 C15 O1 0.8(4) . . . . ?
C16 C14 C15 O2 2.7(3) . . . . ?
C13 C14 C15 O2 -177.8(2) . . . . ?

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
N2 H20 Cl1 0.92(3) 2.11(3) 2.987(2) 158(2) 6_654
O3 H30 Cl1 0.84(4) 2.43(4) 3.266(2) 175(4) .

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Slow evaporation of an acetonitrile solution.'
####################################################################### 
# 
# 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_in063absbeam
_database_code_depnum_ccdc_archive 'CCDC 2016749'
loop_
_audit_author_name
_audit_author_address
'PROFESSOR J D WALLIS'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2020-07-16 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;
_audit_creation_date             2019-04-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
2-Cyano-3-(4?-,8?-bis(dimethylamino)naphthalen-1?-yl)propenenitrile
_chemical_formula_moiety         'C18 H18 N4'
_chemical_formula_sum            'C18 H18 N4'
_chemical_formula_weight         290.36
_chemical_melting_point          378-381
_chemical_oxdiff_formula         'C18 N4 H18'
_chemical_oxdiff_usercomment     'Orange Block '
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           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                   20.7770(7)
_cell_length_b                   9.3348(2)
_cell_length_c                   18.1408(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.584(4)
_cell_angle_gamma                90
_cell_volume                     3199.46(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6879
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      30.5490
_cell_measurement_theta_min      2.4560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-9 -3 25 0.1550
14 2 -25 0.2033
-27 5 10 0.1972
25 -6 -3 0.1495
-12 -11 -4 0.1560
-12 12 2 0.1354
25 0 3 0.1415
-21 0 24 0.1473
-10 6 -15 0.2396
-1 4 23 0.1353
20 -8 -16 0.1229
-8 -1 -20 0.2101

_exptl_crystal_recrystallization_method 
'Slow evaporation from a dichloromethane solution'
_exptl_crystal_size_max          0.543
_exptl_crystal_size_mid          0.415
_exptl_crystal_size_min          0.304
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-9.0000 -3.0000 25.0000 0.9191 -0.3467 0.2317
14.0000 2.0000 -25.0000 -0.9361 0.3260 -0.0309
-27.0000 5.0000 10.0000 0.3997 -0.1302 -0.9041
25.0000 -6.0000 -3.0000 -0.1424 0.0343 0.9920
-12.0000 -11.0000 -4.0000 0.3433 0.9358 -0.0457
-12.0000 12.0000 2.0000 -0.2013 -0.5622 -0.8089
25.0000 -0.0000 3.0000 -0.1536 -0.4742 0.8662
-21.0000 0.0000 24.0000 0.9116 -0.3054 -0.2893
-10.0000 6.0000 -15.0000 -0.5341 0.2066 -0.7995
-1.0000 4.0000 23.0000 0.5630 -0.8273 0.1975
20.0000 -8.0000 -16.0000 -0.4149 0.5745 0.6888
-8.0000 -1.0000 -20.0000 -0.4814 0.7151 -0.5544

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24059
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.434
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  47.00   0.75    7.50    --  -19.97  57.00  30.00  112
  2  ω      1.00  88.00   0.75    7.50    --   20.20  37.00-180.00  116
  3  ω    -49.00  38.00   0.75    7.50    --   20.20 -37.00-180.00  116
  4  ω      7.00  88.00   0.75    7.50    --   20.20  37.00 -30.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0096835000
_diffrn_orient_matrix_UB_12      -0.0313755000
_diffrn_orient_matrix_UB_13      0.0295121000
_diffrn_orient_matrix_UB_21      -0.0157828000
_diffrn_orient_matrix_UB_22      -0.0582067000
_diffrn_orient_matrix_UB_23      -0.0265339000
_diffrn_orient_matrix_UB_31      0.0326654000
_diffrn_orient_matrix_UB_32      -0.0374937000
_diffrn_orient_matrix_UB_33      0.0165285000
_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                6245
_reflns_number_total             7948
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         7948
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0637
_refine_ls_restrained_S_all      1.081
_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)+(0.0456P)²+1.3704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1364
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C33(H33), C4(H4), C26(H26), C15(H15), C22(H22), C25(H25), C7(H7), C8(H8),
 C20(H20), C3(H3), C21(H21), C2(H2)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C29(H29A,H29B,H29C), C31(H31A,H31B,
 H31C), C32(H32A,H32B,H32C), C30(H30A,H30B,H30C), C11(H11A,H11B,H11C), C12(H12A,
 H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.59841(7) 0.57098(16) 0.25036(9) 0.0310(3) Uani 1 1 d . . . . .
N5 N 0.71743(8) 0.10981(15) 0.46511(9) 0.0303(3) Uani 1 1 d . . . . .
N2 N 0.90740(7) 0.37427(16) 0.37136(9) 0.0325(3) Uani 1 1 d . . . . .
N6 N 0.79416(8) 0.66222(16) 0.66500(9) 0.0354(4) Uani 1 1 d . . . . .
C5 C 0.78981(8) 0.47403(17) 0.33936(9) 0.0224(3) Uani 1 1 d . . . . .
N4 N 0.58936(9) 0.05166(18) 0.18391(10) 0.0419(4) Uani 1 1 d . . . . .
N7 N 0.96498(9) 0.0343(2) 0.68593(10) 0.0432(4) Uani 1 1 d . . . . .
C28 C 0.75965(8) 0.33320(17) 0.53646(9) 0.0219(3) Uani 1 1 d . . . . .
N8 N 0.91792(9) -0.10442(19) 0.43944(11) 0.0449(4) Uani 1 1 d . . . . .
C10 C 0.71697(8) 0.48319(16) 0.28548(9) 0.0215(3) Uani 1 1 d . . . . .
C27 C 0.83015(8) 0.29270(17) 0.55054(9) 0.0234(3) Uani 1 1 d . . . . .
C23 C 0.74758(9) 0.46092(17) 0.57156(10) 0.0245(3) Uani 1 1 d . . . . .
C1 C 0.67171(8) 0.57306(17) 0.30578(10) 0.0240(3) Uani 1 1 d . . . . .
C33 C 0.84387(8) 0.17995(18) 0.50227(10) 0.0251(3) Uani 1 1 d . . . . .
H33 H 0.816355 0.179973 0.446648 0.030 Uiso 1 1 calc R . . . .
C19 C 0.70084(9) 0.24598(18) 0.48835(9) 0.0253(3) Uani 1 1 d . . . . .
C34 C 0.89333(9) 0.07648(18) 0.53254(10) 0.0263(4) Uani 1 1 d . . . . .
C9 C 0.68868(9) 0.39474(17) 0.21514(10) 0.0241(3) Uani 1 1 d . . . . .
C6 C 0.83502(8) 0.37734(18) 0.32040(10) 0.0252(3) Uani 1 1 d . . . . .
C35 C 0.93287(9) 0.05393(19) 0.61815(11) 0.0292(4) Uani 1 1 d . . . . .
C4 C 0.81403(9) 0.55558(18) 0.41132(10) 0.0270(4) Uani 1 1 d . . . . .
H4 H 0.861244 0.549221 0.447933 0.032 Uiso 1 1 calc R . . . .
C18 C 0.58189(9) 0.1645(2) 0.15714(11) 0.0310(4) Uani 1 1 d . . . . .
C24 C 0.80733(9) 0.53830(18) 0.62871(10) 0.0276(4) Uani 1 1 d . . . . .
C16 C 0.56997(9) 0.30506(19) 0.12169(10) 0.0301(4) Uani 1 1 d . . . . .
C26 C 0.88540(9) 0.37161(18) 0.60403(10) 0.0286(4) Uani 1 1 d . . . . .
H26 H 0.931467 0.344723 0.614373 0.034 Uiso 1 1 calc R . . . .
C15 C 0.61659(9) 0.41435(19) 0.15199(10) 0.0276(4) Uani 1 1 d . . . . .
H15 H 0.602291 0.506101 0.131873 0.033 Uiso 1 1 calc R . . . .
C22 C 0.67694(9) 0.50786(19) 0.54738(10) 0.0289(4) Uani 1 1 d . . . . .
H22 H 0.668101 0.594935 0.566310 0.035 Uiso 1 1 calc R . . . .
C25 C 0.87435(9) 0.49196(19) 0.64366(11) 0.0307(4) Uani 1 1 d . . . . .
H25 H 0.913191 0.541315 0.680790 0.037 Uiso 1 1 calc R . . . .
C7 C 0.80430(9) 0.28566(19) 0.25560(11) 0.0306(4) Uani 1 1 d . . . . .
H7 H 0.832017 0.216517 0.245813 0.037 Uiso 1 1 calc R . . . .
C36 C 0.90707(9) -0.0233(2) 0.48051(11) 0.0308(4) Uani 1 1 d . . . . .
C8 C 0.73216(9) 0.29453(19) 0.20419(10) 0.0294(4) Uani 1 1 d . . . . .
H8 H 0.713136 0.230430 0.161254 0.035 Uiso 1 1 calc R . . . .
C20 C 0.63325(9) 0.2927(2) 0.46918(10) 0.0319(4) Uani 1 1 d . . . . .
H20 H 0.594962 0.235371 0.437938 0.038 Uiso 1 1 calc R . . . .
C3 C 0.76949(10) 0.64361(19) 0.42820(11) 0.0310(4) Uani 1 1 d . . . . .
H3 H 0.787017 0.698170 0.475367 0.037 Uiso 1 1 calc R . . . .
C21 C 0.62164(9) 0.4266(2) 0.49652(11) 0.0323(4) Uani 1 1 d . . . . .
H21 H 0.575628 0.460564 0.479792 0.039 Uiso 1 1 calc R . . . .
N3 N 0.45009(10) 0.3349(2) -0.00181(12) 0.0595(6) Uani 1 1 d . . . . .
C2 C 0.69786(9) 0.65281(18) 0.37550(11) 0.0297(4) Uani 1 1 d . . . . .
H2 H 0.667979 0.712982 0.387731 0.036 Uiso 1 1 calc R . . . .
C13 C 0.94669(9) 0.5079(2) 0.37729(11) 0.0353(4) Uani 1 1 d . . . . .
H13A H 0.958461 0.515526 0.331564 0.053 Uiso 1 1 calc GR . . . .
H13B H 0.989339 0.507302 0.426375 0.053 Uiso 1 1 calc GR . . . .
H13C H 0.917942 0.588044 0.377789 0.053 Uiso 1 1 calc GR . . . .
C17 C 0.50345(10) 0.3234(2) 0.05271(12) 0.0393(4) Uani 1 1 d . . . . .
C14 C 0.94742(10) 0.2526(2) 0.36171(14) 0.0462(5) Uani 1 1 d . . . . .
H14A H 0.923540 0.165181 0.362858 0.069 Uiso 1 1 calc GR . . . .
H14B H 0.993969 0.252349 0.405107 0.069 Uiso 1 1 calc GR . . . .
H14C H 0.951065 0.260387 0.310812 0.069 Uiso 1 1 calc GR . . . .
C29 C 0.72709(12) -0.0019(2) 0.52483(13) 0.0429(5) Uani 1 1 d . . . . .
H29A H 0.756581 0.033434 0.577943 0.064 Uiso 1 1 calc GR . . . .
H29B H 0.749173 -0.083676 0.512956 0.064 Uiso 1 1 calc GR . . . .
H29C H 0.681875 -0.029170 0.522945 0.064 Uiso 1 1 calc GR . . . .
C31 C 0.76226(12) 0.6360(3) 0.72218(14) 0.0514(6) Uani 1 1 d . . . . .
H31A H 0.725326 0.565969 0.699893 0.077 Uiso 1 1 calc GR . . . .
H31B H 0.742781 0.723684 0.731684 0.077 Uiso 1 1 calc GR . . . .
H31C H 0.797783 0.601161 0.772432 0.077 Uiso 1 1 calc GR . . . .
C32 C 0.85304(12) 0.7620(2) 0.69974(15) 0.0523(6) Uani 1 1 d . . . . .
H32A H 0.888627 0.721524 0.748226 0.078 Uiso 1 1 calc GR . . . .
H32B H 0.836458 0.850420 0.712579 0.078 Uiso 1 1 calc GR . . . .
H32C H 0.872876 0.779714 0.661335 0.078 Uiso 1 1 calc GR . . . .
C30 C 0.67383(14) 0.0652(3) 0.38237(14) 0.0636(7) Uani 1 1 d . . . . .
H30A H 0.628097 0.036217 0.378182 0.095 Uiso 1 1 calc GR . . . .
H30B H 0.696077 -0.013814 0.368238 0.095 Uiso 1 1 calc GR . . . .
H30C H 0.668546 0.143637 0.346096 0.095 Uiso 1 1 calc GR . . . .
C11 C 0.55582(11) 0.4823(4) 0.27849(15) 0.0684(8) Uani 1 1 d . . . . .
H11A H 0.579241 0.392280 0.297474 0.103 Uiso 1 1 calc GR . . . .
H11B H 0.510421 0.465763 0.234673 0.103 Uiso 1 1 calc GR . . . .
H11C H 0.549627 0.530076 0.321949 0.103 Uiso 1 1 calc GR . . . .
C12 C 0.56896(15) 0.7110(3) 0.2216(2) 0.0906(11) Uani 1 1 d . . . . .
H12A H 0.562898 0.761777 0.264291 0.136 Uiso 1 1 calc GR . . . .
H12B H 0.523930 0.700595 0.176228 0.136 Uiso 1 1 calc GR . . . .
H12C H 0.600505 0.763587 0.205185 0.136 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.434(2) . ?
N1 C11 1.451(3) . ?
N1 C12 1.445(3) . ?
N5 C19 1.426(2) . ?
N5 C29 1.456(2) . ?
N5 C30 1.455(2) . ?
N2 C6 1.400(2) . ?
N2 C13 1.470(2) . ?
N2 C14 1.460(2) . ?
N6 C24 1.413(2) . ?
N6 C31 1.465(3) . ?
N6 C32 1.456(2) . ?
C5 C10 1.422(2) . ?
C5 C6 1.444(2) . ?
C5 C4 1.411(2) . ?
N4 C18 1.143(2) . ?
N7 C35 1.144(2) . ?
C28 C27 1.429(2) . ?
C28 C23 1.422(2) . ?
C28 C19 1.425(2) . ?
N8 C36 1.149(2) . ?
C10 C1 1.418(2) . ?
C10 C9 1.425(2) . ?
C27 C33 1.471(2) . ?
C27 C26 1.369(2) . ?
C23 C24 1.438(2) . ?
C23 C22 1.415(2) . ?
C1 C2 1.370(2) . ?
C33 H33 0.9300 . ?
C33 C34 1.350(2) . ?
C19 C20 1.370(2) . ?
C34 C35 1.439(2) . ?
C34 C36 1.437(2) . ?
C9 C15 1.470(2) . ?
C9 C8 1.371(2) . ?
C6 C7 1.377(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.364(2) . ?
C18 C16 1.437(3) . ?
C24 C25 1.373(2) . ?
C16 C15 1.356(2) . ?
C16 C17 1.438(3) . ?
C26 H26 0.9300 . ?
C26 C25 1.403(2) . ?
C15 H15 0.9300 . ?
C22 H22 0.9300 . ?
C22 C21 1.366(2) . ?
C25 H25 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.400(2) . ?
C8 H8 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.403(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.397(3) . ?
C21 H21 0.9300 . ?
N3 C17 1.143(2) . ?
C2 H2 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 112.72(15) . . ?
C1 N1 C12 114.05(16) . . ?
C12 N1 C11 114.5(2) . . ?
C19 N5 C29 113.21(14) . . ?
C19 N5 C30 115.92(16) . . ?
C30 N5 C29 113.35(17) . . ?
C6 N2 C13 116.24(14) . . ?
C6 N2 C14 116.46(16) . . ?
C14 N2 C13 110.00(14) . . ?
C24 N6 C31 115.17(15) . . ?
C24 N6 C32 115.76(16) . . ?
C32 N6 C31 110.27(16) . . ?
C10 C5 C6 119.06(15) . . ?
C4 C5 C10 118.13(14) . . ?
C4 C5 C6 122.74(15) . . ?
C23 C28 C27 120.02(14) . . ?
C23 C28 C19 119.16(14) . . ?
C19 C28 C27 120.81(15) . . ?
C5 C10 C9 120.34(14) . . ?
C1 C10 C5 119.22(15) . . ?
C1 C10 C9 120.27(15) . . ?
C28 C27 C33 121.40(14) . . ?
C26 C27 C28 118.62(15) . . ?
C26 C27 C33 119.60(15) . . ?
C28 C23 C24 118.94(15) . . ?
C22 C23 C28 118.30(15) . . ?
C22 C23 C24 122.75(15) . . ?
C10 C1 N1 115.81(15) . . ?
C2 C1 N1 123.52(15) . . ?
C2 C1 C10 120.65(15) . . ?
C27 C33 H33 117.5 . . ?
C34 C33 C27 124.98(15) . . ?
C34 C33 H33 117.5 . . ?
C28 C19 N5 116.07(14) . . ?
C20 C19 N5 123.83(15) . . ?
C20 C19 C28 120.07(16) . . ?
C33 C34 C35 122.69(16) . . ?
C33 C34 C36 121.50(16) . . ?
C36 C34 C35 115.73(15) . . ?
C10 C9 C15 122.17(14) . . ?
C8 C9 C10 118.28(15) . . ?
C8 C9 C15 119.42(15) . . ?
N2 C6 C5 118.83(15) . . ?
C7 C6 N2 122.67(15) . . ?
C7 C6 C5 118.38(15) . . ?
N7 C35 C34 178.8(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 C5 121.24(16) . . ?
C3 C4 H4 119.4 . . ?
N4 C18 C16 178.0(2) . . ?
N6 C24 C23 118.09(15) . . ?
C25 C24 N6 122.88(15) . . ?
C25 C24 C23 118.99(15) . . ?
C18 C16 C17 115.01(16) . . ?
C15 C16 C18 123.01(16) . . ?
C15 C16 C17 121.95(17) . . ?
C27 C26 H26 119.1 . . ?
C27 C26 C25 121.75(16) . . ?
C25 C26 H26 119.1 . . ?
C9 C15 H15 118.4 . . ?
C16 C15 C9 123.14(16) . . ?
C16 C15 H15 118.4 . . ?
C23 C22 H22 119.7 . . ?
C21 C22 C23 120.67(16) . . ?
C21 C22 H22 119.7 . . ?
C24 C25 C26 121.31(16) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.29(15) . . ?
C8 C7 H7 119.4 . . ?
N8 C36 C34 179.2(2) . . ?
C9 C8 C7 122.09(16) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.19(16) . . ?
C21 C20 H20 119.9 . . ?
C4 C3 H3 119.6 . . ?
C4 C3 C2 120.82(16) . . ?
C2 C3 H3 119.6 . . ?
C22 C21 C20 120.91(16) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C1 C2 C3 119.92(16) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C17 C16 178.4(2) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N5 C29 H29A 109.5 . . ?
N5 C29 H29B 109.5 . . ?
N5 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N6 C31 H31A 109.5 . . ?
N6 C31 H31B 109.5 . . ?
N6 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N6 C32 H32A 109.5 . . ?
N6 C32 H32B 109.5 . . ?
N6 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N5 C30 H30A 109.5 . . ?
N5 C30 H30B 109.5 . . ?
N5 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
N1 C1 C2 C3 176.98(15) . . . . ?
N5 C19 C20 C21 178.09(16) . . . . ?
N2 C6 C7 C8 -177.89(15) . . . . ?
N6 C24 C25 C26 -177.41(16) . . . . ?
C5 C10 C1 N1 -177.03(13) . . . . ?
C5 C10 C1 C2 1.4(2) . . . . ?
C5 C10 C9 C15 -171.22(14) . . . . ?
C5 C10 C9 C8 4.5(2) . . . . ?
C5 C6 C7 C8 6.2(2) . . . . ?
C5 C4 C3 C2 1.7(3) . . . . ?
C28 C27 C33 C34 -137.28(17) . . . . ?
C28 C27 C26 C25 -1.3(2) . . . . ?
C28 C23 C24 N6 -177.88(14) . . . . ?
C28 C23 C24 C25 4.3(2) . . . . ?
C28 C23 C22 C21 5.0(2) . . . . ?
C28 C19 C20 C21 0.2(3) . . . . ?
C10 C5 C6 N2 176.65(14) . . . . ?
C10 C5 C6 C7 -7.3(2) . . . . ?
C10 C5 C4 C3 -1.5(2) . . . . ?
C10 C1 C2 C3 -1.4(2) . . . . ?
C10 C9 C15 C16 -131.19(18) . . . . ?
C10 C9 C8 C7 -5.9(2) . . . . ?
C27 C28 C23 C24 -7.4(2) . . . . ?
C27 C28 C23 C22 171.38(14) . . . . ?
C27 C28 C19 N5 8.1(2) . . . . ?
C27 C28 C19 C20 -173.92(15) . . . . ?
C27 C33 C34 C35 8.1(3) . . . . ?
C27 C33 C34 C36 -175.19(15) . . . . ?
C27 C26 C25 C24 -1.9(3) . . . . ?
C23 C28 C27 C33 -166.86(14) . . . . ?
C23 C28 C27 C26 6.0(2) . . . . ?
C23 C28 C19 N5 -171.06(14) . . . . ?
C23 C28 C19 C20 6.9(2) . . . . ?
C23 C24 C25 C26 0.3(3) . . . . ?
C23 C22 C21 C20 2.2(3) . . . . ?
C1 C10 C9 C15 13.7(2) . . . . ?
C1 C10 C9 C8 -170.56(15) . . . . ?
C33 C27 C26 C25 171.64(15) . . . . ?
C19 C28 C27 C33 14.0(2) . . . . ?
C19 C28 C27 C26 -173.14(14) . . . . ?
C19 C28 C23 C24 171.70(14) . . . . ?
C19 C28 C23 C22 -9.5(2) . . . . ?
C19 C20 C21 C22 -4.9(3) . . . . ?
C9 C10 C1 N1 -1.9(2) . . . . ?
C9 C10 C1 C2 176.59(15) . . . . ?
C6 C5 C10 C1 177.10(14) . . . . ?
C6 C5 C10 C9 2.0(2) . . . . ?
C6 C5 C4 C3 -178.53(15) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C4 C5 C10 C1 0.0(2) . . . . ?
C4 C5 C10 C9 -175.14(14) . . . . ?
C4 C5 C6 N2 -6.4(2) . . . . ?
C4 C5 C6 C7 169.71(15) . . . . ?
C4 C3 C2 C1 -0.2(3) . . . . ?
C18 C16 C15 C9 10.6(3) . . . . ?
C24 C23 C22 C21 -176.18(16) . . . . ?
C26 C27 C33 C34 49.9(2) . . . . ?
C15 C9 C8 C7 170.00(16) . . . . ?
C22 C23 C24 N6 3.4(2) . . . . ?
C22 C23 C24 C25 -174.51(16) . . . . ?
C8 C9 C15 C16 53.1(2) . . . . ?
C13 N2 C6 C5 -62.4(2) . . . . ?
C13 N2 C6 C7 121.72(18) . . . . ?
C17 C16 C15 C9 -171.52(16) . . . . ?
C14 N2 C6 C5 165.48(15) . . . . ?
C14 N2 C6 C7 -10.4(2) . . . . ?
C29 N5 C19 C28 87.41(18) . . . . ?
C29 N5 C19 C20 -90.5(2) . . . . ?
C31 N6 C24 C23 69.2(2) . . . . ?
C31 N6 C24 C25 -113.0(2) . . . . ?
C32 N6 C24 C23 -160.07(17) . . . . ?
C32 N6 C24 C25 17.7(3) . . . . ?
C30 N5 C19 C28 -139.13(19) . . . . ?
C30 N5 C19 C20 43.0(3) . . . . ?
C11 N1 C1 C10 100.6(2) . . . . ?
C11 N1 C1 C2 -77.8(2) . . . . ?
C12 N1 C1 C10 -126.6(2) . . . . ?
C12 N1 C1 C2 54.9(3) . . . . ?

_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 1.045
_oxdiff_exptl_absorpt_empirical_full_min 0.972




####################################################################### 
# 
# 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_jb423absbeam
_database_code_depnum_ccdc_archive 'CCDC 2019629'
loop_
_audit_author_name
_audit_author_address
'PROFESSOR J WALLIS'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2020-07-28 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;
_audit_creation_date             2019-09-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 N2 O2'
_chemical_formula_sum            'C17 H16 N2 O2'
_chemical_formula_weight         280.32
_chemical_melting_point          373-340
_chemical_oxdiff_formula         'C17 H16 O2 N2'
_chemical_oxdiff_usercomment     'Yellow Block'
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      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                   8.6964(8)
_cell_length_b                   9.2214(7)
_cell_length_c                   10.4886(8)
_cell_angle_alpha                102.971(7)
_cell_angle_beta                 101.832(7)
_cell_angle_gamma                113.041(8)
_cell_volume                     712.90(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2531
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      30.3790
_cell_measurement_theta_min      2.5540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 10 4 0.1570
-1 -10 -3 0.1160
-9 0 11 0.2063
9 0 -12 0.1871
-9 7 -7 0.2113
5 -9 11 0.2234
-1 9 -13 0.1465
7 -12 -2 0.0901
12 -4 0 0.2495

_exptl_crystal_recrystallization_method 
'Slow evaporation from a diethyl ether solution.'
_exptl_crystal_size_max          0.475
_exptl_crystal_size_mid          0.406
_exptl_crystal_size_min          0.286
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 10.0000 4.0000 -0.9331 0.2908 0.3108
-1.0000 -10.0000 -3.0000 0.9115 -0.2717 -0.4049
-9.0000 -0.0000 11.0000 -0.3211 0.1169 -0.8959
9.0000 0.0000 -12.0000 0.3846 -0.0893 0.9203
-9.0000 7.0000 -7.0000 0.3466 0.8944 -0.1699
5.0000 -9.0000 11.0000 -0.2970 -0.8981 -0.2882
-1.0000 9.0000 -13.0000 0.2563 0.7665 0.6158
7.0000 -12.0000 -2.0000 0.6483 -0.7532 0.0463
12.0000 -4.0000 -0.0000 -0.2316 -0.7210 0.6726

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8910
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_min         2.551
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -1.00   1.00    2.50    --  -19.89 -62.00  38.11   86
  2  ω    -86.00   0.00   1.00    2.50    --  -19.89 -64.00-134.56   86
  3  ω      3.00  84.00   1.00    2.50    --   20.05  57.00   0.00   81
  4  ω     10.00  56.00   1.00    2.50    --   20.05  57.00-180.00   46
  5  ω      1.00  53.00   1.00    2.50    --   20.05  65.00 -94.72   52
  6  ω    -44.00  17.00   1.00    2.50    --   20.05 -57.00-180.00   61
  7  ω    -41.00   9.00   1.00    2.50    --   20.05 -19.00-120.00   50
  8  ω      0.00  87.00   1.00    2.50    --   20.05  65.00  76.57   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0419341000
_diffrn_orient_matrix_UB_12      -0.0679048000
_diffrn_orient_matrix_UB_13      -0.0635006000
_diffrn_orient_matrix_UB_21      -0.0467113000
_diffrn_orient_matrix_UB_22      0.0401171000
_diffrn_orient_matrix_UB_23      -0.0275926000
_diffrn_orient_matrix_UB_31      0.0696690000
_diffrn_orient_matrix_UB_32      0.0408587000
_diffrn_orient_matrix_UB_33      -0.0244404000
_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                2719
_reflns_number_total             3523
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.044
_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)+(0.0428P)²+0.1525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1135
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C13(H13)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C17(H17A,H17B,H17C)
;
_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 -0.24112(13) 0.23208(13) 0.02615(11) 0.0369(3) Uani 1 1 d . . . . .
O2 O -0.05826(13) 0.14764(12) 0.13419(10) 0.0292(2) Uani 1 1 d . . . . .
N1 N 0.45886(15) 0.53890(14) 0.26254(11) 0.0234(3) Uani 1 1 d . . . . .
N2 N -0.04716(17) 0.66686(16) 0.15325(14) 0.0364(3) Uani 1 1 d . . . . .
C1 C 0.55707(17) 0.67175(16) 0.39203(13) 0.0218(3) Uani 1 1 d . . . . .
C2 C 0.73888(18) 0.75332(18) 0.44243(15) 0.0288(3) Uani 1 1 d . . . . .
H2 H 0.803156 0.718685 0.393214 0.035 Uiso 1 1 calc R . . . .
C3 C 0.82846(19) 0.88915(19) 0.56826(16) 0.0339(4) Uani 1 1 d . . . . .
H3 H 0.951317 0.941050 0.602627 0.041 Uiso 1 1 calc R . . . .
C4 C 0.73769(19) 0.94493(18) 0.63965(15) 0.0316(4) Uani 1 1 d . . . . .
H4 H 0.798946 1.036786 0.720973 0.038 Uiso 1 1 calc R . . . .
C5 C 0.55035(19) 0.86471(17) 0.59165(14) 0.0257(3) Uani 1 1 d . . . . .
C6 C 0.4537(2) 0.92213(18) 0.66417(15) 0.0311(3) Uani 1 1 d . . . . .
H6 H 0.513598 1.014827 0.744926 0.037 Uiso 1 1 calc R . . . .
C7 C 0.2735(2) 0.84313(19) 0.61704(15) 0.0324(3) Uani 1 1 d . . . . .
H7 H 0.211335 0.884741 0.663608 0.039 Uiso 1 1 calc R . . . .
C8 C 0.18135(19) 0.69882(18) 0.49813(15) 0.0277(3) Uani 1 1 d . . . . .
H8 H 0.058406 0.645220 0.467933 0.033 Uiso 1 1 calc R . . . .
C9 C 0.26902(17) 0.63513(16) 0.42545(13) 0.0216(3) Uani 1 1 d . . . . .
C10 C 0.45825(17) 0.72172(16) 0.46830(13) 0.0212(3) Uani 1 1 d . . . . .
C11 C 0.5374(2) 0.42917(19) 0.22354(17) 0.0346(4) Uani 1 1 d . . . . .
H11A H 0.635345 0.485971 0.194486 0.052 Uiso 1 1 calc GR . . . .
H11B H 0.450468 0.329266 0.148891 0.052 Uiso 1 1 calc GR . . . .
H11C H 0.578095 0.400055 0.301588 0.052 Uiso 1 1 calc GR . . . .
C12 C 0.4120(2) 0.59985(19) 0.15047(15) 0.0312(3) Uani 1 1 d . . . . .
H12A H 0.357914 0.669363 0.177471 0.047 Uiso 1 1 calc GR . . . .
H12B H 0.330600 0.506324 0.068703 0.047 Uiso 1 1 calc GR . . . .
H12C H 0.516800 0.663832 0.131755 0.047 Uiso 1 1 calc GR . . . .
C13 C 0.16377(17) 0.47063(17) 0.31412(14) 0.0224(3) Uani 1 1 d . . . . .
H13 H 0.196775 0.386739 0.317786 0.027 Uiso 1 1 calc R . . . .
C14 C 0.02271(17) 0.43474(17) 0.20749(14) 0.0234(3) Uani 1 1 d . . . . .
C15 C -0.01583(17) 0.56486(17) 0.17870(14) 0.0266(3) Uani 1 1 d . . . . .
C16 C -0.10636(18) 0.26336(18) 0.11141(14) 0.0253(3) Uani 1 1 d . . . . .
C17 C -0.1847(2) -0.02357(18) 0.04995(17) 0.0355(4) Uani 1 1 d . . . . .
H17A H -0.194175 -0.038941 -0.045465 0.053 Uiso 1 1 calc GR . . . .
H17B H -0.297997 -0.046619 0.060694 0.053 Uiso 1 1 calc GR . . . .
H17C H -0.145588 -0.098605 0.078784 0.053 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.2026(16) . ?
O2 C16 1.3393(16) . ?
O2 C17 1.4487(17) . ?
N1 C1 1.4259(17) . ?
N1 C11 1.4586(18) . ?
N1 C12 1.4639(17) . ?
N2 C15 1.1462(18) . ?
C1 C2 1.3759(18) . ?
C1 C10 1.4203(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.411(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.355(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.417(2) . ?
C5 C6 1.413(2) . ?
C5 C10 1.4271(19) . ?
C6 H6 0.9300 . ?
C6 C7 1.363(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.407(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(2) . ?
C9 C10 1.4334(18) . ?
C9 C13 1.4772(19) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.3485(18) . ?
C14 C15 1.4420(18) . ?
C14 C16 1.4851(19) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C16 O2 C17 114.87(11) . . ?
C1 N1 C11 115.60(11) . . ?
C1 N1 C12 111.86(11) . . ?
C11 N1 C12 110.93(12) . . ?
C2 C1 N1 123.15(13) . . ?
C2 C1 C10 120.01(13) . . ?
C10 C1 N1 116.82(11) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.44(14) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.81(14) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.66(14) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C10 119.00(14) . . ?
C6 C5 C4 121.39(13) . . ?
C6 C5 C10 119.61(13) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.69(14) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.19(14) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.49(14) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 119.31(13) . . ?
C8 C9 C13 117.89(12) . . ?
C10 C9 C13 122.53(12) . . ?
C1 C10 C5 118.90(12) . . ?
C1 C10 C9 122.56(12) . . ?
C5 C10 C9 118.54(13) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13 118.0 . . ?
C14 C13 C9 123.96(12) . . ?
C14 C13 H13 118.0 . . ?
C13 C14 C15 121.31(13) . . ?
C13 C14 C16 124.71(12) . . ?
C15 C14 C16 113.98(11) . . ?
N2 C15 C14 178.73(16) . . ?
O1 C16 O2 124.10(13) . . ?
O1 C16 C14 123.68(13) . . ?
O2 C16 C14 112.18(11) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
N1 C1 C2 C3 176.98(12) . . . . ?
N1 C1 C10 C5 -173.86(11) . . . . ?
N1 C1 C10 C9 5.45(18) . . . . ?
C1 C2 C3 C4 -2.0(2) . . . . ?
C2 C1 C10 C5 4.62(18) . . . . ?
C2 C1 C10 C9 -176.07(12) . . . . ?
C2 C3 C4 C5 2.0(2) . . . . ?
C3 C4 C5 C6 -179.44(13) . . . . ?
C3 C4 C5 C10 1.3(2) . . . . ?
C4 C5 C6 C7 -179.68(13) . . . . ?
C4 C5 C10 C1 -4.57(18) . . . . ?
C4 C5 C10 C9 176.09(11) . . . . ?
C5 C6 C7 C8 2.6(2) . . . . ?
C6 C5 C10 C1 176.19(12) . . . . ?
C6 C5 C10 C9 -3.15(18) . . . . ?
C6 C7 C8 C9 -1.0(2) . . . . ?
C7 C8 C9 C10 -2.72(19) . . . . ?
C7 C8 C9 C13 171.48(12) . . . . ?
C8 C9 C10 C1 -174.62(12) . . . . ?
C8 C9 C10 C5 4.70(18) . . . . ?
C8 C9 C13 C14 55.15(18) . . . . ?
C9 C13 C14 C15 12.5(2) . . . . ?
C9 C13 C14 C16 -166.72(13) . . . . ?
C10 C1 C2 C3 -1.4(2) . . . . ?
C10 C5 C6 C7 -0.5(2) . . . . ?
C10 C9 C13 C14 -130.85(14) . . . . ?
C11 N1 C1 C2 34.45(18) . . . . ?
C11 N1 C1 C10 -147.12(12) . . . . ?
C12 N1 C1 C2 -93.79(15) . . . . ?
C12 N1 C1 C10 84.64(14) . . . . ?
C13 C9 C10 C1 11.46(19) . . . . ?
C13 C9 C10 C5 -169.23(11) . . . . ?
C13 C14 C16 O1 171.91(14) . . . . ?
C13 C14 C16 O2 -5.9(2) . . . . ?
C15 C14 C16 O1 -7.4(2) . . . . ?
C15 C14 C16 O2 174.82(12) . . . . ?
C17 O2 C16 O1 -1.7(2) . . . . ?
C17 O2 C16 C14 176.05(12) . . . . ?

_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 1.061
_oxdiff_exptl_absorpt_empirical_full_min 0.934
