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

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

data_jb_stacey2cnabs
_database_code_depnum_ccdc_archive 'CCDC 2069108'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 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)-4,5-diphenylnaphthalen-1-yl)-

_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         'C28 H21 N3'
_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'

_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                   8.6981(5)
_cell_length_b                   12.6447(6)
_cell_length_c                   12.8788(7)
_cell_angle_alpha                81.679(4)
_cell_angle_beta                 77.685(4)
_cell_angle_gamma                78.768(4)
_cell_volume                     1349.48(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5362
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.8800
_cell_measurement_theta_min      3.6690
_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  0.904
_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    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_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 3 0.0534
0 16 -5 0.0958
-1 -13 -13 0.0280
1 13 14 0.0762
12 6 8 0.1580
-12 -5 -5 0.1855
0 -8 -16 0.0445
0 8 16 0.0842
-12 -5 -7 0.1716

_exptl_crystal_recrystallization_method 
'Slow evaporation from a toluene solution.'
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.107
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 3.0000 -0.9811 0.1314 0.2034
0.0000 16.0000 -5.0000 0.9812 -0.1186 -0.0825
-1.0000 -13.0001 -13.0000 -0.3459 0.0520 0.9074
1.0000 13.0001 14.0000 0.3193 -0.0543 -0.9575
12.0000 5.9999 8.0000 0.1343 0.9363 -0.3667
-12.0000 -4.9999 -5.0000 -0.1611 -0.9514 0.1959
-0.0000 -8.0001 -16.0000 0.0014 0.1018 0.9667
0.0000 8.0001 16.0000 -0.0014 -0.1018 -0.9667
-12.0000 -4.9999 -7.0000 -0.1079 -0.9468 0.2959

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0447
_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       -16
_diffrn_reflns_number            23451
_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         3.257
_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 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00   0.00   1.00   27.50    --  -19.97 -65.00  28.68   86
  2  ω      1.00  87.00   1.00   27.50    --   20.05  64.00-170.94   86
  3  ω      3.00  87.00   1.00   27.50    --   20.05  57.00 -90.00   84
  4  ω      3.00  87.00   1.00   27.50    --   20.05  57.00 120.00   84
  5  ω      3.00  87.00   1.00   27.50    --   20.05  57.00  30.00   84
  6  ω      2.00  87.00   1.00   27.50    --   20.05  62.00 -28.22   85
  7  ω      0.00  87.00   1.00   27.50    --   20.05  65.00 -58.46   87
  8  ω    -47.00  37.00   1.00   27.50    --   20.05 -57.00   0.00   84
  9  ω      1.00  71.00   1.00   27.50    --   20.05  65.00  66.02   70
;
_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      0.0024180000
_diffrn_orient_matrix_UB_12      0.0530155000
_diffrn_orient_matrix_UB_13      -0.0265952000
_diffrn_orient_matrix_UB_21      0.0836261000
_diffrn_orient_matrix_UB_22      -0.0081331000
_diffrn_orient_matrix_UB_23      -0.0022972000
_diffrn_orient_matrix_UB_31      0.0131838000
_diffrn_orient_matrix_UB_32      -0.0207912000
_diffrn_orient_matrix_UB_33      -0.0500252000
_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                4808
_reflns_number_total             6693
_reflns_odcompleteness_completeness 99.76
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         6693
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0522
_refine_ls_restrained_S_all      1.030
_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)+(0.0461P)²+0.4020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1233
_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), 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   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
N1 N 0.84453(16) 0.33601(10) 0.27752(10) 0.0293(3) Uani 1 1 d . . . . .
N2 N 0.65432(17) 0.60513(12) 0.01356(11) 0.0375(3) Uani 1 1 d . . . . .
N3 N 0.29735(17) 0.48906(11) 0.28206(12) 0.0373(3) Uani 1 1 d . . . . .
C1 C 0.85244(17) 0.22118(12) 0.30094(11) 0.0240(3) Uani 1 1 d . . . . .
C2 C 0.97050(18) 0.15304(13) 0.34373(12) 0.0301(4) Uani 1 1 d . . . . .
H2 H 1.057134 0.179247 0.355905 0.036 Uiso 1 1 calc R . . . .
C3 C 0.95922(17) 0.04308(13) 0.36903(12) 0.0276(3) Uani 1 1 d . . . . .
H3 H 1.042590 -0.003142 0.395363 0.033 Uiso 1 1 calc R . . . .
C4 C 0.83131(16) -0.00063(12) 0.35710(10) 0.0209(3) Uani 1 1 d . . . . .
C5 C 0.70837(16) 0.06807(11) 0.30714(10) 0.0190(3) Uani 1 1 d . . . . .
C6 C 0.57214(16) 0.03490(11) 0.28244(10) 0.0203(3) Uani 1 1 d . . . . .
C7 C 0.46345(17) 0.11064(12) 0.23563(11) 0.0235(3) Uani 1 1 d . . . . .
H7 H 0.370456 0.089932 0.226946 0.028 Uiso 1 1 calc R . . . .
C8 C 0.48684(16) 0.21733(12) 0.20057(11) 0.0225(3) Uani 1 1 d . . . . .
H8 H 0.412963 0.265154 0.166377 0.027 Uiso 1 1 calc R . . . .
C9 C 0.61963(16) 0.25074(11) 0.21708(10) 0.0203(3) Uani 1 1 d . . . . .
C10 C 0.72591(16) 0.17931(11) 0.27629(10) 0.0199(3) Uani 1 1 d . . . . .
C11 C 0.9979(2) 0.37310(16) 0.23722(17) 0.0494(5) Uani 1 1 d . . . . .
H11A H 1.054230 0.366820 0.294894 0.074 Uiso 1 1 calc GR . . . .
H11B H 0.979459 0.447493 0.207301 0.074 Uiso 1 1 calc GR . . . .
H11C H 1.060356 0.329308 0.183056 0.074 Uiso 1 1 calc GR . . . .
C12 C 0.7457(2) 0.39723(14) 0.36285(13) 0.0378(4) Uani 1 1 d . . . . .
H12A H 0.646712 0.370401 0.386894 0.057 Uiso 1 1 calc GR . . . .
H12B H 0.724415 0.472554 0.336402 0.057 Uiso 1 1 calc GR . . . .
H12C H 0.800866 0.389018 0.421369 0.057 Uiso 1 1 calc GR . . . .
C13 C 0.83332(16) -0.11716(12) 0.39976(11) 0.0217(3) Uani 1 1 d . . . . .
C14 C 0.96194(18) -0.19438(13) 0.36087(12) 0.0277(3) Uani 1 1 d . . . . .
H14 H 1.042846 -0.172997 0.306719 0.033 Uiso 1 1 calc R . . . .
C15 C 0.97174(19) -0.30287(13) 0.40147(13) 0.0319(4) Uani 1 1 d . . . . .
H15 H 1.058085 -0.353644 0.374158 0.038 Uiso 1 1 calc R . . . .
C16 C 0.8526(2) -0.33512(13) 0.48268(12) 0.0319(4) Uani 1 1 d . . . . .
H16 H 0.858291 -0.407732 0.509908 0.038 Uiso 1 1 calc R . . . .
C17 C 0.72487(19) -0.25910(13) 0.52329(11) 0.0278(3) Uani 1 1 d . . . . .
H17 H 0.645262 -0.280695 0.578335 0.033 Uiso 1 1 calc R . . . .
C18 C 0.71488(17) -0.15094(12) 0.48242(11) 0.0227(3) Uani 1 1 d . . . . .
H18 H 0.628562 -0.100436 0.510276 0.027 Uiso 1 1 calc R . . . .
C19 C 0.54030(16) -0.07895(11) 0.30122(11) 0.0210(3) Uani 1 1 d . . . . .
C20 C 0.64375(18) -0.16181(12) 0.24925(11) 0.0262(3) Uani 1 1 d . . . . .
H20 H 0.735890 -0.146938 0.202067 0.031 Uiso 1 1 calc R . . . .
C21 C 0.6103(2) -0.26634(13) 0.26737(13) 0.0338(4) Uani 1 1 d . . . . .
H21 H 0.680512 -0.321460 0.232797 0.041 Uiso 1 1 calc R . . . .
C22 C 0.4724(2) -0.28915(13) 0.33696(14) 0.0361(4) Uani 1 1 d . . . . .
H22 H 0.451205 -0.359676 0.350058 0.043 Uiso 1 1 calc R . . . .
C23 C 0.36698(19) -0.20706(13) 0.38656(13) 0.0321(4) Uani 1 1 d . . . . .
H23 H 0.273553 -0.221909 0.432208 0.038 Uiso 1 1 calc R . . . .
C24 C 0.40004(17) -0.10250(13) 0.36848(12) 0.0259(3) Uani 1 1 d . . . . .
H24 H 0.327827 -0.047288 0.401597 0.031 Uiso 1 1 calc R . . . .
C25 C 0.66691(18) 0.35248(12) 0.15853(11) 0.0234(3) Uani 1 1 d . . . . .
H25 H 0.7672(18) 0.3439(12) 0.1059(12) 0.021(4) Uiso 1 1 d . . . . .
C26 C 0.56798(17) 0.44945(12) 0.15335(11) 0.0243(3) Uani 1 1 d . . . . .
C27 C 0.61505(18) 0.53680(13) 0.07613(12) 0.0270(3) Uani 1 1 d . . . . .
C28 C 0.41664(19) 0.47067(12) 0.22435(12) 0.0268(3) Uani 1 1 d . . . . .
C29 C 0.7760(2) 0.16611(15) -0.04713(13) 0.0375(4) Uani 1 1 d . . . . .
C30 C 0.7914(2) 0.26344(15) -0.10868(14) 0.0439(4) Uani 1 1 d . . . . .
H30 H 0.718233 0.292942 -0.152648 0.053 Uiso 1 1 calc R . . . .
C31 C 0.9104(3) 0.31684(19) -0.10647(16) 0.0587(6) Uani 1 1 d . . . . .
H31 H 0.918008 0.382511 -0.148685 0.070 Uiso 1 1 calc R . . . .
C32 C 1.0205(3) 0.2753(2) -0.0426(2) 0.0692(8) Uani 1 1 d . . . . .
H32 H 1.103204 0.311833 -0.041745 0.083 Uiso 1 1 calc R . . . .
C33 C 1.0058(3) 0.1763(2) 0.02163(19) 0.0670(7) Uani 1 1 d . . . . .
H33 H 1.079043 0.146651 0.065512 0.080 Uiso 1 1 calc R . . . .
C34 C 0.8821(2) 0.12336(16) 0.01909(14) 0.0470(5) Uani 1 1 d . . . . .
H34 H 0.870748 0.058695 0.062353 0.056 Uiso 1 1 calc R . . . .
C35 C 0.6423(3) 0.1081(2) -0.05304(18) 0.0664(7) Uani 1 1 d . . . . .
H35A H 0.655142 0.088790 -0.124178 0.100 Uiso 1 1 calc GR . . . .
H35B H 0.541648 0.154917 -0.035290 0.100 Uiso 1 1 calc GR . . . .
H35C H 0.645203 0.043604 -0.003412 0.100 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 1.4308(19) . ?
N1 C11 1.465(2) . ?
N1 C12 1.460(2) . ?
N2 C27 1.1439(19) . ?
N3 C28 1.145(2) . ?
C1 C2 1.364(2) . ?
C1 C10 1.4202(19) . ?
C2 C3 1.399(2) . ?
C3 C4 1.380(2) . ?
C4 C5 1.4430(18) . ?
C4 C13 1.4944(19) . ?
C5 C6 1.4402(18) . ?
C5 C10 1.4338(19) . ?
C6 C7 1.3776(19) . ?
C6 C19 1.4946(19) . ?
C7 C8 1.3987(19) . ?
C8 C9 1.3706(19) . ?
C9 C10 1.4242(19) . ?
C9 C25 1.4784(19) . ?
C13 C14 1.390(2) . ?
C13 C18 1.3961(19) . ?
C14 C15 1.389(2) . ?
C15 C16 1.383(2) . ?
C16 C17 1.383(2) . ?
C17 C18 1.386(2) . ?
C19 C20 1.391(2) . ?
C19 C24 1.3940(19) . ?
C20 C21 1.385(2) . ?
C21 C22 1.388(2) . ?
C22 C23 1.377(2) . ?
C23 C24 1.384(2) . ?
C25 C26 1.356(2) . ?
C26 C27 1.4358(19) . ?
C26 C28 1.436(2) . ?
C29 C30 1.378(2) . ?
C29 C34 1.371(3) . ?
C29 C35 1.511(3) . ?
C30 C31 1.349(3) . ?
C31 C32 1.373(3) . ?
C32 C33 1.410(3) . ?
C33 C34 1.381(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 115.70(14) . . ?
C1 N1 C12 113.55(12) . . ?
C12 N1 C11 112.18(14) . . ?
C2 C1 N1 124.56(13) . . ?
C2 C1 C10 120.11(13) . . ?
C10 C1 N1 115.34(12) . . ?
C1 C2 C3 118.95(14) . . ?
C4 C3 C2 123.67(14) . . ?
C3 C4 C5 118.67(13) . . ?
C3 C4 C13 115.44(12) . . ?
C5 C4 C13 125.88(12) . . ?
C6 C5 C4 126.24(13) . . ?
C10 C5 C4 116.90(12) . . ?
C10 C5 C6 116.83(12) . . ?
C5 C6 C19 124.50(12) . . ?
C7 C6 C5 119.45(13) . . ?
C7 C6 C19 116.02(12) . . ?
C6 C7 C8 122.87(13) . . ?
C9 C8 C7 119.40(13) . . ?
C8 C9 C10 119.79(13) . . ?
C8 C9 C25 119.83(12) . . ?
C10 C9 C25 119.56(12) . . ?
C1 C10 C5 121.21(12) . . ?
C1 C10 C9 117.74(12) . . ?
C9 C10 C5 121.02(12) . . ?
C14 C13 C4 119.31(12) . . ?
C14 C13 C18 118.34(13) . . ?
C18 C13 C4 122.23(13) . . ?
C15 C14 C13 121.16(14) . . ?
C16 C15 C14 119.75(15) . . ?
C17 C16 C15 119.83(15) . . ?
C16 C17 C18 120.38(14) . . ?
C17 C18 C13 120.54(14) . . ?
C20 C19 C6 121.63(12) . . ?
C20 C19 C24 118.69(13) . . ?
C24 C19 C6 119.60(13) . . ?
C21 C20 C19 120.37(14) . . ?
C20 C21 C22 120.23(16) . . ?
C23 C22 C21 119.84(15) . . ?
C22 C23 C24 120.02(15) . . ?
C23 C24 C19 120.79(15) . . ?
C26 C25 C9 124.75(13) . . ?
C25 C26 C27 119.91(13) . . ?
C25 C26 C28 122.72(13) . . ?
C28 C26 C27 117.36(13) . . ?
N2 C27 C26 178.82(19) . . ?
N3 C28 C26 178.48(17) . . ?
C30 C29 C35 119.72(18) . . ?
C34 C29 C30 119.43(18) . . ?
C34 C29 C35 120.85(19) . . ?
C31 C30 C29 121.3(2) . . ?
C30 C31 C32 120.7(2) . . ?
C31 C32 C33 118.7(2) . . ?
C34 C33 C32 119.7(2) . . ?
C29 C34 C33 120.1(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 176.07(14) . . . . ?
N1 C1 C10 C5 -172.52(12) . . . . ?
N1 C1 C10 C9 9.30(19) . . . . ?
C1 C2 C3 C4 -2.6(2) . . . . ?
C2 C1 C10 C5 7.6(2) . . . . ?
C2 C1 C10 C9 -170.61(14) . . . . ?
C2 C3 C4 C5 5.7(2) . . . . ?
C2 C3 C4 C13 -173.52(14) . . . . ?
C3 C4 C5 C6 176.04(13) . . . . ?
C3 C4 C5 C10 -2.01(19) . . . . ?
C3 C4 C13 C14 -58.17(18) . . . . ?
C3 C4 C13 C18 117.80(15) . . . . ?
C4 C5 C6 C7 179.19(13) . . . . ?
C4 C5 C6 C19 -2.6(2) . . . . ?
C4 C5 C10 C1 -4.39(19) . . . . ?
C4 C5 C10 C9 173.73(12) . . . . ?
C4 C13 C14 C15 177.30(13) . . . . ?
C4 C13 C18 C17 -176.90(13) . . . . ?
C5 C4 C13 C14 122.69(15) . . . . ?
C5 C4 C13 C18 -61.34(19) . . . . ?
C5 C6 C7 C8 6.6(2) . . . . ?
C5 C6 C19 C20 -62.74(19) . . . . ?
C5 C6 C19 C24 120.33(15) . . . . ?
C6 C5 C10 C1 177.37(12) . . . . ?
C6 C5 C10 C9 -4.51(19) . . . . ?
C6 C7 C8 C9 -3.0(2) . . . . ?
C6 C19 C20 C21 -179.32(13) . . . . ?
C6 C19 C24 C23 179.46(13) . . . . ?
C7 C6 C19 C20 115.50(15) . . . . ?
C7 C6 C19 C24 -61.43(17) . . . . ?
C7 C8 C9 C10 -4.5(2) . . . . ?
C7 C8 C9 C25 165.05(13) . . . . ?
C8 C9 C10 C1 -173.54(13) . . . . ?
C8 C9 C10 C5 8.3(2) . . . . ?
C8 C9 C25 C26 51.0(2) . . . . ?
C9 C25 C26 C27 -166.23(13) . . . . ?
C9 C25 C26 C28 15.3(2) . . . . ?
C10 C1 C2 C3 -4.0(2) . . . . ?
C10 C5 C6 C7 -2.75(19) . . . . ?
C10 C5 C6 C19 175.43(12) . . . . ?
C10 C9 C25 C26 -139.40(15) . . . . ?
C11 N1 C1 C2 36.9(2) . . . . ?
C11 N1 C1 C10 -143.03(15) . . . . ?
C12 N1 C1 C2 -94.95(18) . . . . ?
C12 N1 C1 C10 85.15(16) . . . . ?
C13 C4 C5 C6 -4.8(2) . . . . ?
C13 C4 C5 C10 177.10(13) . . . . ?
C13 C14 C15 C16 -0.6(2) . . . . ?
C14 C13 C18 C17 -0.9(2) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C15 C16 C17 C18 0.6(2) . . . . ?
C16 C17 C18 C13 0.0(2) . . . . ?
C18 C13 C14 C15 1.2(2) . . . . ?
C19 C6 C7 C8 -171.68(13) . . . . ?
C19 C20 C21 C22 0.6(2) . . . . ?
C20 C19 C24 C23 2.4(2) . . . . ?
C20 C21 C22 C23 1.2(2) . . . . ?
C21 C22 C23 C24 -1.2(2) . . . . ?
C22 C23 C24 C19 -0.7(2) . . . . ?
C24 C19 C20 C21 -2.4(2) . . . . ?
C25 C9 C10 C1 16.85(19) . . . . ?
C25 C9 C10 C5 -161.33(13) . . . . ?
C29 C30 C31 C32 0.2(3) . . . . ?
C30 C29 C34 C33 -1.8(3) . . . . ?
C30 C31 C32 C33 -0.7(3) . . . . ?
C31 C32 C33 C34 0.0(3) . . . . ?
C32 C33 C34 C29 1.2(3) . . . . ?
C34 C29 C30 C31 1.1(3) . . . . ?
C35 C29 C30 C31 -179.15(18) . . . . ?
C35 C29 C34 C33 178.48(18) . . . . ?

_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 1.046
_oxdiff_exptl_absorpt_empirical_full_min 0.938
####################################################################### 
# 
# 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_jb317abs
_database_code_depnum_ccdc_archive 'CCDC 2069094'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 downloaded from the CCDC.
;
_audit_creation_date             2019-10-01
_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        
;
1,2,3,4-Tetrahydro-1,2,2-trimethyl-spiro[cyclopentan-1,3-acenaphth[5,6-bc]azepine]-2,5-dione
;
_chemical_formula_moiety         'C20 H19 N O2'
_chemical_formula_sum            'C20 H19 N O2'
_chemical_formula_weight         305.36
_chemical_melting_point          453-456
_chemical_oxdiff_formula         'C20 H19 N1 O2'
_chemical_oxdiff_usercomment     'Pale 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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7625(5)
_cell_length_b                   32.3176(10)
_cell_length_c                   8.6130(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.945(4)
_cell_angle_gamma                90
_cell_volume                     2959.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2832
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      28.3900
_cell_measurement_theta_min      2.4570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.940
_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    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
13 -2 4 0.0527
5 28 -9 0.1132
-5 -28 9 0.1132
-6 28 9 0.1157
6 -28 -9 0.1157
-8 5 11 0.0603
-14 -2 -3 0.0135

_exptl_crystal_preparation       
'Prepared from a slow evaporation of a dichloromethane / hexane solution.'
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.082
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
13.0022 -2.0013 4.0002 0.9218 -0.3166 -0.0821
5.0002 27.9995 -9.0003 -0.1432 0.0616 -0.9742
-5.0002 -27.9995 9.0003 0.1432 -0.0616 0.9742
-6.0008 28.0007 9.0002 0.2926 0.9254 0.2546
6.0008 -28.0007 -9.0002 -0.2926 -0.9254 -0.2546
-8.0008 5.0009 11.0003 0.2156 0.6526 0.7161
-14.0023 -1.9986 -3.0002 -0.9331 0.3083 0.2131

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14496
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.377
_diffrn_reflns_theta_min         2.293
_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 0.839
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  13.00   1.00  100.00    --  -16.16  57.00  60.00   27
  2  ω    -42.00  21.00   1.00  100.00    --   16.24 -57.00 120.00   63
  3  ω    -49.00  81.00   1.00  100.00    --   16.24   0.00 150.00  130
;
_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      0.0538776000
_diffrn_orient_matrix_UB_12      0.0036310000
_diffrn_orient_matrix_UB_13      0.0571388000
_diffrn_orient_matrix_UB_21      -0.0307126000
_diffrn_orient_matrix_UB_22      0.0170766000
_diffrn_orient_matrix_UB_23      0.0292202000
_diffrn_orient_matrix_UB_31      -0.0247146000
_diffrn_orient_matrix_UB_32      -0.0132921000
_diffrn_orient_matrix_UB_33      0.0531642000
_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                4795
_reflns_number_total             6829
_reflns_odcompleteness_completeness 99.92
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6829
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1484
_refine_ls_R_factor_gt           0.1040
_refine_ls_restrained_S_all      1.150
_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)+(0.0486P)²+4.8426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1877
_refine_ls_wR_factor_ref         0.2072
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B), C16(H16A,H16B), C18(H18A,
 H18B), C19(H19A,H19B), C31(H31A,H31B), C32(H32A,H32B), C34(H34A,H34B),
 C36(H36A,H36B), C38(H38A,H38B), C39(H39A,H39B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C22(H22), C23(H23), C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C33(H33A,H33B,H33C)
;
_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 0.2295(2) 0.38727(9) -0.0294(3) 0.0407(7) Uani 1 1 d . . . . .
O2 O 0.0044(2) 0.49041(7) 0.1829(3) 0.0263(6) Uani 1 1 d . . . . .
N1 N 0.2255(3) 0.44288(9) 0.4344(3) 0.0222(6) Uani 1 1 d . . . . .
C1 C 0.3571(3) 0.44411(10) 0.4798(4) 0.0205(7) Uani 1 1 d . . . . .
C2 C 0.4150(3) 0.44122(11) 0.6344(4) 0.0223(7) Uani 1 1 d . . . . .
H2 H 0.364542 0.439869 0.712636 0.027 Uiso 1 1 calc R . . . .
C3 C 0.5470(3) 0.44022(11) 0.6795(4) 0.0242(8) Uani 1 1 d . . . . .
H3 H 0.581765 0.439067 0.785203 0.029 Uiso 1 1 calc R . . . .
C4 C 0.6228(3) 0.44097(10) 0.5666(4) 0.0195(7) Uani 1 1 d . . . . .
C5 C 0.5654(3) 0.44407(10) 0.4091(4) 0.0193(7) Uani 1 1 d . . . . .
C6 C 0.6551(3) 0.44447(9) 0.3047(4) 0.0181(7) Uani 1 1 d . . . . .
C7 C 0.6135(3) 0.44933(10) 0.1481(4) 0.0205(7) Uani 1 1 d . . . . .
H7 H 0.669752 0.448727 0.076361 0.025 Uiso 1 1 calc R . . . .
C8 C 0.4837(3) 0.45529(10) 0.0962(4) 0.0196(7) Uani 1 1 d . . . . .
H8 H 0.456888 0.459180 -0.010728 0.023 Uiso 1 1 calc R . . . .
C9 C 0.3946(3) 0.45568(10) 0.1948(4) 0.0172(7) Uani 1 1 d . . . . .
C10 C 0.4350(3) 0.44778(9) 0.3590(4) 0.0183(7) Uani 1 1 d . . . . .
C11 C 0.7641(3) 0.43932(12) 0.5734(4) 0.0258(8) Uani 1 1 d . . . . .
H11A H 0.798653 0.414722 0.628576 0.031 Uiso 1 1 calc R . . . .
H11B H 0.803638 0.463509 0.626564 0.031 Uiso 1 1 calc R . . . .
C12 C 0.7849(3) 0.43832(11) 0.3992(4) 0.0245(8) Uani 1 1 d . . . . .
H12A H 0.841337 0.460302 0.378073 0.029 Uiso 1 1 calc R . . . .
H12B H 0.820143 0.411978 0.374015 0.029 Uiso 1 1 calc R . . . .
C13 C 0.1482(4) 0.44281(13) 0.5595(4) 0.0317(9) Uani 1 1 d . . . . .
H13A H 0.158601 0.416965 0.614945 0.048 Uiso 1 1 calc GR . . . .
H13B H 0.061489 0.446316 0.514650 0.048 Uiso 1 1 calc GR . . . .
H13C H 0.173816 0.465087 0.631042 0.048 Uiso 1 1 calc GR . . . .
C14 C 0.1832(3) 0.41532(10) 0.3035(4) 0.0216(7) Uani 1 1 d . . . . .
H14A H 0.106730 0.401581 0.322148 0.026 Uiso 1 1 calc R . . . .
H14B H 0.246586 0.394215 0.299020 0.026 Uiso 1 1 calc R . . . .
C16 C 0.2624(3) 0.46918(10) 0.1324(4) 0.0193(7) Uani 1 1 d . . . . .
H16A H 0.259128 0.476827 0.022966 0.023 Uiso 1 1 calc R . . . .
H16B H 0.244546 0.493917 0.188845 0.023 Uiso 1 1 calc R . . . .
C15 C 0.1574(3) 0.43789(10) 0.1428(4) 0.0196(7) Uani 1 1 d . . . . .
C17 C 0.1431(3) 0.40570(11) 0.0117(4) 0.0218(7) Uani 1 1 d . . . . .
C18 C 0.0081(3) 0.40055(13) -0.0583(5) 0.0353(10) Uani 1 1 d . . . . .
H18A H -0.018810 0.372264 -0.045708 0.042 Uiso 1 1 calc R . . . .
H18B H -0.004064 0.407067 -0.169606 0.042 Uiso 1 1 calc R . . . .
C19 C -0.0671(3) 0.43024(11) 0.0285(4) 0.0243(8) Uani 1 1 d . . . . .
H19A H -0.124477 0.446464 -0.045611 0.029 Uiso 1 1 calc R . . . .
H19B H -0.115551 0.415052 0.095641 0.029 Uiso 1 1 calc R . . . .
C20 C 0.0274(3) 0.45791(10) 0.1254(4) 0.0189(7) Uani 1 1 d . . . . .
O3 O -0.2736(3) 0.35396(9) -0.1336(3) 0.0412(7) Uani 1 1 d . . . . .
O4 O -0.4940(3) 0.26133(9) 0.1377(4) 0.0441(8) Uani 1 1 d . . . . .
N2 N -0.2766(3) 0.32025(10) 0.3511(4) 0.0300(7) Uani 1 1 d . . . . .
C21 C -0.1458(4) 0.31911(11) 0.3966(5) 0.0293(9) Uani 1 1 d . . . . .
C22 C -0.0896(4) 0.32791(12) 0.5523(5) 0.0377(10) Uani 1 1 d . . . . .
H22 H -0.140464 0.334298 0.626932 0.045 Uiso 1 1 calc R . . . .
C23 C 0.0417(4) 0.32721(13) 0.5967(5) 0.0400(10) Uani 1 1 d . . . . .
H23 H 0.076554 0.331686 0.701123 0.048 Uiso 1 1 calc R . . . .
C24 C 0.1190(4) 0.31992(12) 0.4865(5) 0.0372(10) Uani 1 1 d . . . . .
C25 C 0.0630(4) 0.31044(11) 0.3340(5) 0.0323(9) Uani 1 1 d . . . . .
C26 C 0.1546(4) 0.30119(11) 0.2359(5) 0.0356(10) Uani 1 1 d . . . . .
C27 C 0.1144(4) 0.28903(12) 0.0885(5) 0.0382(10) Uani 1 1 d . . . . .
H27 H 0.172082 0.283840 0.020914 0.046 Uiso 1 1 calc R . . . .
C28 C -0.0173(4) 0.28399(12) 0.0346(5) 0.0365(10) Uani 1 1 d . . . . .
H28 H -0.043470 0.275119 -0.068008 0.044 Uiso 1 1 calc R . . . .
C29 C -0.1061(3) 0.29173(11) 0.1283(5) 0.0291(8) Uani 1 1 d . . . . .
C30 C -0.0657(3) 0.30821(10) 0.2854(4) 0.0230(8) Uani 1 1 d . . . . .
C31 C 0.2601(4) 0.31791(14) 0.4993(6) 0.0491(12) Uani 1 1 d . . . . .
H31A H 0.294703 0.296744 0.573540 0.059 Uiso 1 1 calc R . . . .
H31B H 0.298135 0.344312 0.532559 0.059 Uiso 1 1 calc R . . . .
C32 C 0.2827(4) 0.30688(13) 0.3291(6) 0.0454(11) Uani 1 1 d . . . . .
H32A H 0.327197 0.329064 0.285509 0.054 Uiso 1 1 calc R . . . .
H32B H 0.331560 0.281653 0.329397 0.054 Uiso 1 1 calc R . . . .
C33 C -0.3563(4) 0.32737(12) 0.4708(5) 0.0357(10) Uani 1 1 d . . . . .
H33A H -0.333543 0.308390 0.556234 0.054 Uiso 1 1 calc GR . . . .
H33B H -0.442731 0.323158 0.425965 0.054 Uiso 1 1 calc GR . . . .
H33C H -0.345025 0.355237 0.508944 0.054 Uiso 1 1 calc GR . . . .
C34 C -0.3160(4) 0.34051(11) 0.2018(4) 0.0267(8) Uani 1 1 d . . . . .
H34A H -0.251159 0.359822 0.182490 0.032 Uiso 1 1 calc R . . . .
H34B H -0.391838 0.356288 0.207750 0.032 Uiso 1 1 calc R . . . .
C36 C -0.2390(3) 0.27736(11) 0.0750(4) 0.0270(8) Uani 1 1 d . . . . .
H36A H -0.258275 0.256221 0.147630 0.032 Uiso 1 1 calc R . . . .
H36B H -0.242322 0.264322 -0.026972 0.032 Uiso 1 1 calc R . . . .
C35 C -0.3421(3) 0.30993(11) 0.0618(4) 0.0239(8) Uani 1 1 d . . . . .
C37 C -0.3576(3) 0.33544(11) -0.0876(4) 0.0250(8) Uani 1 1 d . . . . .
C38 C -0.4903(4) 0.33414(17) -0.1683(6) 0.0527(13) Uani 1 1 d . . . . .
H38A H -0.495077 0.320195 -0.268736 0.063 Uiso 1 1 calc R . . . .
H38B H -0.522561 0.362023 -0.186859 0.063 Uiso 1 1 calc R . . . .
C39 C -0.5662(4) 0.31119(13) -0.0645(5) 0.0392(10) Uani 1 1 d . . . . .
H39A H -0.620688 0.291117 -0.124900 0.047 Uiso 1 1 calc R . . . .
H39B H -0.617630 0.330197 -0.014776 0.047 Uiso 1 1 calc R . . . .
C40 C -0.4724(4) 0.28993(11) 0.0565(5) 0.0308(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.203(4) . ?
O2 C20 1.203(4) . ?
N1 C1 1.410(4) . ?
N1 C13 1.460(4) . ?
N1 C14 1.453(4) . ?
C1 C2 1.382(5) . ?
C1 C10 1.438(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.413(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.363(4) . ?
C4 C5 1.404(5) . ?
C4 C11 1.514(5) . ?
C5 C6 1.418(4) . ?
C5 C10 1.408(5) . ?
C6 C7 1.363(5) . ?
C6 C12 1.516(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.412(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(4) . ?
C9 C10 1.437(4) . ?
C9 C16 1.505(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.552(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.551(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.529(4) . ?
C15 C17 1.525(5) . ?
C15 C20 1.528(4) . ?
C17 C18 1.494(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.524(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.505(5) . ?
O3 C37 1.202(4) . ?
O4 C40 1.203(4) . ?
N2 C21 1.402(5) . ?
N2 C33 1.458(5) . ?
N2 C34 1.447(5) . ?
C21 C22 1.411(5) . ?
C21 C30 1.429(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.406(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.376(6) . ?
C24 C25 1.391(6) . ?
C24 C31 1.508(6) . ?
C25 C26 1.426(5) . ?
C25 C30 1.385(5) . ?
C26 C27 1.335(6) . ?
C26 C32 1.495(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.431(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.366(5) . ?
C29 C30 1.456(5) . ?
C29 C36 1.506(5) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.564(7) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 C35 1.551(5) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C35 1.520(5) . ?
C35 C37 1.515(5) . ?
C35 C40 1.539(5) . ?
C37 C38 1.488(6) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C38 C39 1.498(6) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C40 1.500(6) . ?

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 117.3(3) . . ?
C1 N1 C14 114.4(3) . . ?
C14 N1 C13 115.2(3) . . ?
N1 C1 C10 118.3(3) . . ?
C2 C1 N1 123.2(3) . . ?
C2 C1 C10 118.4(3) . . ?
C1 C2 H2 118.3 . . ?
C1 C2 C3 123.3(3) . . ?
C3 C2 H2 118.3 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 117.9(3) . . ?
C3 C4 C11 132.9(3) . . ?
C5 C4 C11 109.2(3) . . ?
C4 C5 C6 111.8(3) . . ?
C4 C5 C10 124.7(3) . . ?
C10 C5 C6 123.4(3) . . ?
C5 C6 C12 108.7(3) . . ?
C7 C6 C5 118.5(3) . . ?
C7 C6 C12 132.8(3) . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 119.1(3) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 H8 118.1 . . ?
C9 C8 C7 123.8(3) . . ?
C9 C8 H8 118.1 . . ?
C8 C9 C10 118.2(3) . . ?
C8 C9 C16 119.6(3) . . ?
C10 C9 C16 121.8(3) . . ?
C5 C10 C1 115.9(3) . . ?
C5 C10 C9 116.8(3) . . ?
C9 C10 C1 127.3(3) . . ?
C4 C11 H11A 110.8 . . ?
C4 C11 H11B 110.8 . . ?
C4 C11 C12 105.0(3) . . ?
H11A C11 H11B 108.8 . . ?
C12 C11 H11A 110.8 . . ?
C12 C11 H11B 110.8 . . ?
C6 C12 C11 104.9(3) . . ?
C6 C12 H12A 110.8 . . ?
C6 C12 H12B 110.8 . . ?
C11 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
H12A C12 H12B 108.8 . . ?
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 108.9 . . ?
N1 C14 H14B 108.9 . . ?
N1 C14 C15 113.3(3) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C9 C16 H16A 108.1 . . ?
C9 C16 H16B 108.1 . . ?
C9 C16 C15 117.0(3) . . ?
H16A C16 H16B 107.3 . . ?
C15 C16 H16A 108.1 . . ?
C15 C16 H16B 108.1 . . ?
C16 C15 C14 109.4(3) . . ?
C17 C15 C14 108.9(3) . . ?
C17 C15 C16 113.5(3) . . ?
C17 C15 C20 103.3(3) . . ?
C20 C15 C14 108.7(3) . . ?
C20 C15 C16 112.8(3) . . ?
O1 C17 C15 124.2(3) . . ?
O1 C17 C18 125.0(3) . . ?
C18 C17 C15 110.8(3) . . ?
C17 C18 H18A 110.4 . . ?
C17 C18 H18B 110.4 . . ?
C17 C18 C19 106.8(3) . . ?
H18A C18 H18B 108.6 . . ?
C19 C18 H18A 110.4 . . ?
C19 C18 H18B 110.4 . . ?
C18 C19 H19A 110.5 . . ?
C18 C19 H19B 110.5 . . ?
H19A C19 H19B 108.6 . . ?
C20 C19 C18 106.4(3) . . ?
C20 C19 H19A 110.5 . . ?
C20 C19 H19B 110.5 . . ?
O2 C20 C15 124.9(3) . . ?
O2 C20 C19 125.7(3) . . ?
C19 C20 C15 109.4(3) . . ?
C21 N2 C33 118.8(3) . . ?
C21 N2 C34 113.8(3) . . ?
C34 N2 C33 115.7(3) . . ?
N2 C21 C22 121.6(3) . . ?
N2 C21 C30 120.2(3) . . ?
C22 C21 C30 118.2(4) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.3(4) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.3(4) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C25 118.0(4) . . ?
C23 C24 C31 131.8(4) . . ?
C25 C24 C31 110.1(4) . . ?
C24 C25 C26 111.6(4) . . ?
C30 C25 C24 124.2(4) . . ?
C30 C25 C26 124.1(4) . . ?
C25 C26 C32 108.7(4) . . ?
C27 C26 C25 118.3(4) . . ?
C27 C26 C32 133.0(4) . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.0(4) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 118.8 . . ?
C29 C28 C27 122.4(4) . . ?
C29 C28 H28 118.8 . . ?
C28 C29 C30 118.7(4) . . ?
C28 C29 C36 118.8(4) . . ?
C30 C29 C36 121.9(3) . . ?
C21 C30 C29 126.1(3) . . ?
C25 C30 C21 117.6(3) . . ?
C25 C30 C29 116.1(3) . . ?
C24 C31 H31A 110.9 . . ?
C24 C31 H31B 110.9 . . ?
C24 C31 C32 104.0(3) . . ?
H31A C31 H31B 109.0 . . ?
C32 C31 H31A 110.9 . . ?
C32 C31 H31B 110.9 . . ?
C26 C32 C31 105.5(3) . . ?
C26 C32 H32A 110.6 . . ?
C26 C32 H32B 110.6 . . ?
C31 C32 H32A 110.6 . . ?
C31 C32 H32B 110.6 . . ?
H32A C32 H32B 108.8 . . ?
N2 C33 H33A 109.5 . . ?
N2 C33 H33B 109.5 . . ?
N2 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N2 C34 H34A 108.9 . . ?
N2 C34 H34B 108.9 . . ?
N2 C34 C35 113.3(3) . . ?
H34A C34 H34B 107.7 . . ?
C35 C34 H34A 108.9 . . ?
C35 C34 H34B 108.9 . . ?
C29 C36 H36A 108.0 . . ?
C29 C36 H36B 108.0 . . ?
C29 C36 C35 117.2(3) . . ?
H36A C36 H36B 107.3 . . ?
C35 C36 H36A 108.0 . . ?
C35 C36 H36B 108.0 . . ?
C36 C35 C34 110.0(3) . . ?
C36 C35 C40 111.3(3) . . ?
C37 C35 C34 107.2(3) . . ?
C37 C35 C36 115.0(3) . . ?
C37 C35 C40 102.9(3) . . ?
C40 C35 C34 110.1(3) . . ?
O3 C37 C35 124.1(3) . . ?
O3 C37 C38 125.2(4) . . ?
C38 C37 C35 110.7(3) . . ?
C37 C38 H38A 110.1 . . ?
C37 C38 H38B 110.1 . . ?
C37 C38 C39 107.9(4) . . ?
H38A C38 H38B 108.4 . . ?
C39 C38 H38A 110.1 . . ?
C39 C38 H38B 110.1 . . ?
C38 C39 H39A 110.6 . . ?
C38 C39 H39B 110.6 . . ?
C38 C39 C40 105.7(3) . . ?
H39A C39 H39B 108.7 . . ?
C40 C39 H39A 110.6 . . ?
C40 C39 H39B 110.6 . . ?
O4 C40 C35 124.3(4) . . ?
O4 C40 C39 125.9(4) . . ?
C39 C40 C35 109.9(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
O1 C17 C18 C19 -179.3(4) . . . . ?
N1 C1 C2 C3 176.5(3) . . . . ?
N1 C1 C10 C5 -172.9(3) . . . . ?
N1 C1 C10 C9 8.6(5) . . . . ?
N1 C14 C15 C16 42.7(4) . . . . ?
N1 C14 C15 C17 167.2(3) . . . . ?
N1 C14 C15 C20 -80.9(3) . . . . ?
C1 N1 C14 C15 -97.1(3) . . . . ?
C1 C2 C3 C4 -1.9(5) . . . . ?
C2 C1 C10 C5 5.9(5) . . . . ?
C2 C1 C10 C9 -172.6(3) . . . . ?
C2 C3 C4 C5 2.0(5) . . . . ?
C2 C3 C4 C11 -178.4(4) . . . . ?
C3 C4 C5 C6 -179.9(3) . . . . ?
C3 C4 C5 C10 2.1(5) . . . . ?
C3 C4 C11 C12 176.0(4) . . . . ?
C4 C5 C6 C7 -177.0(3) . . . . ?
C4 C5 C6 C12 3.9(4) . . . . ?
C4 C5 C10 C1 -6.1(5) . . . . ?
C4 C5 C10 C9 172.6(3) . . . . ?
C4 C11 C12 C6 6.4(4) . . . . ?
C5 C4 C11 C12 -4.3(4) . . . . ?
C5 C6 C7 C8 2.3(5) . . . . ?
C5 C6 C12 C11 -6.4(4) . . . . ?
C6 C5 C10 C1 176.2(3) . . . . ?
C6 C5 C10 C9 -5.2(5) . . . . ?
C6 C7 C8 C9 -1.4(5) . . . . ?
C7 C6 C12 C11 174.7(4) . . . . ?
C7 C8 C9 C10 -2.8(5) . . . . ?
C7 C8 C9 C16 169.9(3) . . . . ?
C8 C9 C10 C1 -175.7(3) . . . . ?
C8 C9 C10 C5 5.8(4) . . . . ?
C8 C9 C16 C15 120.9(3) . . . . ?
C9 C16 C15 C14 41.1(4) . . . . ?
C9 C16 C15 C17 -80.6(4) . . . . ?
C9 C16 C15 C20 162.3(3) . . . . ?
C10 C1 C2 C3 -2.3(5) . . . . ?
C10 C5 C6 C7 1.1(5) . . . . ?
C10 C5 C6 C12 -178.1(3) . . . . ?
C10 C9 C16 C15 -66.6(4) . . . . ?
C11 C4 C5 C6 0.4(4) . . . . ?
C11 C4 C5 C10 -177.6(3) . . . . ?
C12 C6 C7 C8 -178.8(3) . . . . ?
C13 N1 C1 C2 6.4(5) . . . . ?
C13 N1 C1 C10 -174.8(3) . . . . ?
C13 N1 C14 C15 122.6(3) . . . . ?
C14 N1 C1 C2 -133.0(3) . . . . ?
C14 N1 C1 C10 45.8(4) . . . . ?
C14 C15 C17 O1 -75.9(4) . . . . ?
C14 C15 C17 C18 104.5(3) . . . . ?
C14 C15 C20 O2 81.0(4) . . . . ?
C14 C15 C20 C19 -97.7(3) . . . . ?
C16 C9 C10 C1 11.7(5) . . . . ?
C16 C9 C10 C5 -166.8(3) . . . . ?
C16 C15 C17 O1 46.2(5) . . . . ?
C16 C15 C17 C18 -133.5(3) . . . . ?
C16 C15 C20 O2 -40.5(4) . . . . ?
C16 C15 C20 C19 140.7(3) . . . . ?
C15 C17 C18 C19 0.3(4) . . . . ?
C17 C15 C20 O2 -163.5(3) . . . . ?
C17 C15 C20 C19 17.8(3) . . . . ?
C17 C18 C19 C20 10.8(4) . . . . ?
C18 C19 C20 O2 163.1(3) . . . . ?
C18 C19 C20 C15 -18.2(4) . . . . ?
C20 C15 C17 O1 168.7(3) . . . . ?
C20 C15 C17 C18 -11.0(4) . . . . ?
O3 C37 C38 C39 -174.6(4) . . . . ?
N2 C21 C22 C23 -179.2(4) . . . . ?
N2 C21 C30 C25 175.5(3) . . . . ?
N2 C21 C30 C29 -9.7(5) . . . . ?
N2 C34 C35 C36 -43.6(4) . . . . ?
N2 C34 C35 C37 -169.4(3) . . . . ?
N2 C34 C35 C40 79.3(4) . . . . ?
C21 N2 C34 C35 96.4(4) . . . . ?
C21 C22 C23 C24 3.3(6) . . . . ?
C22 C21 C30 C25 -5.4(5) . . . . ?
C22 C21 C30 C29 169.4(3) . . . . ?
C22 C23 C24 C25 -4.5(6) . . . . ?
C22 C23 C24 C31 179.2(4) . . . . ?
C23 C24 C25 C26 -176.4(3) . . . . ?
C23 C24 C25 C30 0.6(6) . . . . ?
C23 C24 C31 C32 178.1(4) . . . . ?
C24 C25 C26 C27 176.0(4) . . . . ?
C24 C25 C26 C32 -2.8(4) . . . . ?
C24 C25 C30 C21 4.4(5) . . . . ?
C24 C25 C30 C29 -170.9(3) . . . . ?
C24 C31 C32 C26 -3.0(4) . . . . ?
C25 C24 C31 C32 1.5(4) . . . . ?
C25 C26 C27 C28 -2.5(6) . . . . ?
C25 C26 C32 C31 3.6(4) . . . . ?
C26 C25 C30 C21 -179.0(3) . . . . ?
C26 C25 C30 C29 5.7(5) . . . . ?
C26 C27 C28 C29 0.9(6) . . . . ?
C27 C26 C32 C31 -174.9(4) . . . . ?
C27 C28 C29 C30 4.0(6) . . . . ?
C27 C28 C29 C36 -167.4(3) . . . . ?
C28 C29 C30 C21 178.2(3) . . . . ?
C28 C29 C30 C25 -7.0(5) . . . . ?
C28 C29 C36 C35 -123.6(4) . . . . ?
C29 C36 C35 C34 -40.3(4) . . . . ?
C29 C36 C35 C37 80.9(4) . . . . ?
C29 C36 C35 C40 -162.6(3) . . . . ?
C30 C21 C22 C23 1.8(6) . . . . ?
C30 C25 C26 C27 -1.0(6) . . . . ?
C30 C25 C26 C32 -179.8(3) . . . . ?
C30 C29 C36 C35 65.3(5) . . . . ?
C31 C24 C25 C26 0.7(5) . . . . ?
C31 C24 C25 C30 177.7(3) . . . . ?
C32 C26 C27 C28 175.9(4) . . . . ?
C33 N2 C21 C22 -5.1(5) . . . . ?
C33 N2 C21 C30 173.9(3) . . . . ?
C33 N2 C34 C35 -120.8(4) . . . . ?
C34 N2 C21 C22 136.5(4) . . . . ?
C34 N2 C21 C30 -44.6(4) . . . . ?
C34 C35 C37 O3 69.2(4) . . . . ?
C34 C35 C37 C38 -111.0(4) . . . . ?
C34 C35 C40 O4 -80.5(4) . . . . ?
C34 C35 C40 C39 99.9(3) . . . . ?
C36 C29 C30 C21 -10.8(5) . . . . ?
C36 C29 C30 C25 164.1(3) . . . . ?
C36 C35 C37 O3 -53.5(5) . . . . ?
C36 C35 C37 C38 126.3(4) . . . . ?
C36 C35 C40 O4 41.7(5) . . . . ?
C36 C35 C40 C39 -137.9(3) . . . . ?
C35 C37 C38 C39 5.6(5) . . . . ?
C37 C35 C40 O4 165.4(3) . . . . ?
C37 C35 C40 C39 -14.1(4) . . . . ?
C37 C38 C39 C40 -14.1(5) . . . . ?
C38 C39 C40 O4 -161.7(4) . . . . ?
C38 C39 C40 C35 17.8(4) . . . . ?
C40 C35 C37 O3 -174.7(3) . . . . ?
C40 C35 C37 C38 5.1(4) . . . . ?

_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 1.044
_oxdiff_exptl_absorpt_empirical_full_min 0.966
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/hexane'
####################################################################### 
# 
# 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_jb264absbeam
_database_code_depnum_ccdc_archive 'CCDC 2069095'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 downloaded from the CCDC.
;
_audit_creation_date             2019-09-11
_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        
;
4,5-diiodo-9,9-dimethyl-9H-fluorene
;
_chemical_formula_moiety         'C15 H12 I2'
_chemical_formula_sum            'C15 H12 I2'
_chemical_formula_weight         446.05
_chemical_melting_point          323-326
_chemical_oxdiff_formula         'C15 H12 I2'
_chemical_oxdiff_usercomment     'Pale Yellow 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'
I I -0.4742 1.8119 '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                   8.4109(2)
_cell_length_b                   9.6735(3)
_cell_length_c                   17.0655(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.496(2)
_cell_angle_gamma                90
_cell_volume                     1388.45(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3895
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      28.9290
_cell_measurement_theta_min      2.4000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.506
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_correction_T_min  0.432
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.134
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -24 0.0235
0 1 24 0.0235
-5 12 0 0.1197
5 -12 0 0.1197
-12 0 5 0.0828
12 0 -5 0.0828
6 11 4 0.1237
-6 -11 -4 0.1237

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/petrol (40-60)'
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.047
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
0.0099 -0.9850 -24.0443 -0.8618 -0.2415 -0.4503
-0.0099 0.9850 24.0443 0.8618 0.2415 0.4503
-5.0399 12.0310 0.0109 -0.3674 -0.1168 0.8997
5.0399 -12.0310 -0.0109 0.3674 0.1168 -0.8997
-12.0326 0.0016 4.9765 0.2404 -0.8942 0.4597
12.0326 -0.0016 -4.9765 -0.2404 0.8942 -0.4597
5.9895 11.0209 4.0455 -0.2354 0.7583 0.5554
-5.9895 -11.0209 -4.0455 0.2354 -0.7583 -0.5554

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6967
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.387
_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 1.000
_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     34.00  85.00   1.00   12.50    --   16.24  37.00  90.00   51
  2  ω     19.00  46.00   1.00   12.50    --   16.24 -19.00-180.00   27
  3  ω    -50.00  12.00   1.00   12.50    --   16.24 -57.00 -30.00   62
  4  ω    -48.00  27.00   1.00   12.50    --   16.24 -57.00 120.00   75
  5  ω    -54.00 -22.00   1.00   12.50    --   16.24 -19.00-180.00   32
;
_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      -0.0046087000
_diffrn_orient_matrix_UB_12      -0.0325017000
_diffrn_orient_matrix_UB_13      0.0371728000
_diffrn_orient_matrix_UB_21      0.0781002000
_diffrn_orient_matrix_UB_22      0.0230040000
_diffrn_orient_matrix_UB_23      0.0091357000
_diffrn_orient_matrix_UB_31      -0.0315026000
_diffrn_orient_matrix_UB_32      0.0615668000
_diffrn_orient_matrix_UB_33      0.0161944000
_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                2477
_reflns_number_total             2837
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (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         0.959
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2837
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.050
_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)+(0.0256P)²+0.0995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0613
_refine_ls_wR_factor_ref         0.0646
_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), C9(H9), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_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
I1 I 0.97953(3) 0.30715(3) 0.65371(2) 0.02499(10) Uani 1 1 d . . . . .
I2 I 0.81735(3) 0.60258(3) 0.54794(2) 0.02243(9) Uani 1 1 d . . . . .
C1 C 0.9020(5) 0.4212(4) 0.7519(2) 0.0154(8) Uani 1 1 d . . . . .
C2 C 0.9945(5) 0.3955(4) 0.8183(3) 0.0222(9) Uani 1 1 d . . . . .
H2 H 1.092261 0.351814 0.813006 0.027 Uiso 1 1 calc R . . . .
C3 C 0.9435(5) 0.4339(4) 0.8924(2) 0.0227(9) Uani 1 1 d . . . . .
H3 H 1.009471 0.420975 0.935790 0.027 Uiso 1 1 calc R . . . .
C4 C 0.7944(5) 0.4915(4) 0.9013(2) 0.0195(9) Uani 1 1 d . . . . .
H4 H 0.756682 0.512436 0.950983 0.023 Uiso 1 1 calc R . . . .
C5 C 0.7017(4) 0.5178(4) 0.8354(2) 0.0137(8) Uani 1 1 d . . . . .
C6 C 0.7576(4) 0.4930(4) 0.7584(2) 0.0129(8) Uani 1 1 d . . . . .
C7 C 0.6316(4) 0.5418(4) 0.7026(2) 0.0135(8) Uani 1 1 d . . . . .
C8 C 0.6222(5) 0.5706(4) 0.6223(2) 0.0144(8) Uani 1 1 d . . . . .
C9 C 0.4756(5) 0.6037(4) 0.5878(2) 0.0209(9) Uani 1 1 d . . . . .
H9 H 0.469105 0.616666 0.533866 0.025 Uiso 1 1 calc R . . . .
C10 C 0.3393(5) 0.6175(4) 0.6328(2) 0.0188(9) Uani 1 1 d . . . . .
H10 H 0.241179 0.633184 0.608915 0.023 Uiso 1 1 calc R . . . .
C11 C 0.3514(5) 0.6077(4) 0.7139(2) 0.0194(9) Uani 1 1 d . . . . .
H11 H 0.263341 0.624469 0.745118 0.023 Uiso 1 1 calc R . . . .
C12 C 0.4962(5) 0.5727(4) 0.7477(2) 0.0140(8) Uani 1 1 d . . . . .
C13 C 0.5322(4) 0.5675(4) 0.8344(2) 0.0147(8) Uani 1 1 d . . . . .
C14 C 0.4239(5) 0.4656(4) 0.8779(2) 0.0251(10) Uani 1 1 d . . . . .
H14A H 0.315779 0.496863 0.874460 0.038 Uiso 1 1 calc GR . . . .
H14B H 0.456027 0.460701 0.931988 0.038 Uiso 1 1 calc GR . . . .
H14C H 0.432418 0.375693 0.854548 0.038 Uiso 1 1 calc GR . . . .
C15 C 0.5185(5) 0.7130(4) 0.8713(2) 0.0238(9) Uani 1 1 d . . . . .
H15A H 0.581101 0.777346 0.841894 0.036 Uiso 1 1 calc GR . . . .
H15B H 0.556645 0.710128 0.924503 0.036 Uiso 1 1 calc GR . . . .
H15C H 0.409301 0.741831 0.870560 0.036 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
I1 C1 2.114(4) . ?
I2 C8 2.106(4) . ?
C1 C2 1.391(5) . ?
C1 C6 1.405(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(5) . ?
C5 C6 1.420(5) . ?
C5 C13 1.504(5) . ?
C6 C7 1.496(5) . ?
C7 C8 1.400(5) . ?
C7 C12 1.413(5) . ?
C8 C9 1.399(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.392(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(5) . ?
C12 C13 1.508(5) . ?
C13 C14 1.538(5) . ?
C13 C15 1.547(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C2 C1 I1 112.3(3) . . ?
C2 C1 C6 120.1(3) . . ?
C6 C1 I1 126.4(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.3(4) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 C13 126.5(3) . . ?
C6 C5 C13 111.4(3) . . ?
C1 C6 C5 116.7(3) . . ?
C1 C6 C7 135.6(3) . . ?
C5 C6 C7 107.3(3) . . ?
C8 C7 C6 136.0(3) . . ?
C8 C7 C12 116.9(3) . . ?
C12 C7 C6 106.9(3) . . ?
C7 C8 I2 125.6(3) . . ?
C9 C8 I2 113.7(3) . . ?
C9 C8 C7 120.0(4) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.1(4) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.2(4) . . ?
C12 C11 H11 120.4 . . ?
C7 C12 C13 111.8(3) . . ?
C11 C12 C7 122.3(4) . . ?
C11 C12 C13 125.8(4) . . ?
C5 C13 C12 101.8(3) . . ?
C5 C13 C14 110.8(3) . . ?
C5 C13 C15 111.1(3) . . ?
C12 C13 C14 112.4(3) . . ?
C12 C13 C15 110.7(3) . . ?
C14 C13 C15 109.8(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
I1 C1 C2 C3 -165.0(3) . . . . ?
I1 C1 C6 C5 157.0(3) . . . . ?
I1 C1 C6 C7 -15.5(6) . . . . ?
I2 C8 C9 C10 -166.0(3) . . . . ?
C1 C2 C3 C4 3.8(6) . . . . ?
C1 C6 C7 C8 -21.5(7) . . . . ?
C1 C6 C7 C12 163.7(4) . . . . ?
C2 C1 C6 C5 -9.3(5) . . . . ?
C2 C1 C6 C7 178.3(4) . . . . ?
C2 C3 C4 C5 -3.9(6) . . . . ?
C3 C4 C5 C6 -2.8(6) . . . . ?
C3 C4 C5 C13 174.0(4) . . . . ?
C4 C5 C6 C1 9.3(5) . . . . ?
C4 C5 C6 C7 -176.2(3) . . . . ?
C4 C5 C13 C12 -178.6(4) . . . . ?
C4 C5 C13 C14 -58.9(5) . . . . ?
C4 C5 C13 C15 63.5(5) . . . . ?
C5 C6 C7 C8 165.6(4) . . . . ?
C5 C6 C7 C12 -9.2(4) . . . . ?
C6 C1 C2 C3 3.1(6) . . . . ?
C6 C5 C13 C12 -1.4(4) . . . . ?
C6 C5 C13 C14 118.3(3) . . . . ?
C6 C5 C13 C15 -119.4(3) . . . . ?
C6 C7 C8 I2 -16.9(6) . . . . ?
C6 C7 C8 C9 174.1(4) . . . . ?
C6 C7 C12 C11 -173.4(3) . . . . ?
C6 C7 C12 C13 8.7(4) . . . . ?
C7 C8 C9 C10 4.3(6) . . . . ?
C7 C12 C13 C5 -4.7(4) . . . . ?
C7 C12 C13 C14 -123.2(4) . . . . ?
C7 C12 C13 C15 113.6(3) . . . . ?
C8 C7 C12 C11 10.7(5) . . . . ?
C8 C7 C12 C13 -167.3(3) . . . . ?
C8 C9 C10 C11 4.5(6) . . . . ?
C9 C10 C11 C12 -5.5(5) . . . . ?
C10 C11 C12 C7 -2.2(6) . . . . ?
C10 C11 C12 C13 175.5(3) . . . . ?
C11 C12 C13 C5 177.5(3) . . . . ?
C11 C12 C13 C14 58.9(5) . . . . ?
C11 C12 C13 C15 -64.3(5) . . . . ?
C12 C7 C8 I2 157.5(3) . . . . ?
C12 C7 C8 C9 -11.5(5) . . . . ?
C13 C5 C6 C1 -167.9(3) . . . . ?
C13 C5 C6 C7 6.5(4) . . . . ?

_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 1.104
_oxdiff_exptl_absorpt_empirical_full_min 0.928
####################################################################### 
# 
# 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_jb315abs
_database_code_depnum_ccdc_archive 'CCDC 2069092'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-29
_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        
1,2,3,4-Tetrahydro-1,2,2-trimethyl-spiro[1,3-dioxane-5,3-acenaphth[5,6-bc]azepine]-4,6-dione
_chemical_formula_moiety         'C21 H21 N O4'
_chemical_formula_sum            'C21 H21 N O4'
_chemical_formula_weight         351.39
_chemical_melting_point          471-474
_chemical_oxdiff_formula         'C21 H21 O4 N1'
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.4257(3)
_cell_length_b                   8.8243(3)
_cell_length_c                   18.7805(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.546(3)
_cell_angle_gamma                90
_cell_volume                     1692.83(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2680
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      27.8630
_cell_measurement_theta_min      3.9970
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -12 6 0.1637
-14 -2 6 0.1659
1 -3 -26 0.1099
-2 2 26 0.0674
13 6 -8 0.1361
-12 -7 4 0.1665
-3 12 -3 0.0633
9 -10 -1 0.1036

_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.19
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
-0.0053 -11.9894 6.0034 0.1997 0.8202 -0.5196
-13.9629 -2.0008 5.9919 -0.0544 -0.3548 -0.8949
0.9874 -3.0015 -25.9632 -0.9838 0.2604 0.0252
-1.9854 2.0021 25.9640 0.9613 -0.2265 -0.1232
12.9673 5.9971 -7.9932 -0.0321 0.0466 1.0116
-11.9717 -6.9967 3.9995 -0.1037 0.0600 -0.9823
-2.9860 11.9892 -3.0078 -0.1446 -0.9270 0.3394
8.9703 -9.9900 -0.9879 0.1161 1.0016 0.0966

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7351
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.230
_diffrn_reflns_theta_min         3.379
_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 0.835
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  54.00   1.00   22.50    --  -13.67  57.00 120.00   80
  2  ω    -11.00  34.00   1.00   22.50    --  -13.67  57.00-120.00   45
  3  ω    -74.00 -30.00   1.00   22.50    --  -13.67 -37.00  30.00   44
  4  ω      7.00  55.00   1.00   22.50    --  -13.67  37.00  30.00   48
;
_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      0.0199909000
_diffrn_orient_matrix_UB_12      0.0025392000
_diffrn_orient_matrix_UB_13      0.0383583000
_diffrn_orient_matrix_UB_21      0.0349499000
_diffrn_orient_matrix_UB_22      -0.0688028000
_diffrn_orient_matrix_UB_23      -0.0007465000
_diffrn_orient_matrix_UB_31      0.0565930000
_diffrn_orient_matrix_UB_32      0.0415005000
_diffrn_orient_matrix_UB_33      -0.0036163000
_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                2736
_reflns_number_total             3489
_reflns_odcompleteness_completeness 99.63
_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    ?
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         3489
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.094
_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)+(0.0386P)²+0.3273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1132
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O4-C18 \\sim O4A-C18
 with sigma of 0.02
 O4-C19 \\sim O4A-C19A
 with sigma of 0.02
 O3-C17 \\sim O3A-C17
 with sigma of 0.02
 O3-C19 \\sim O3A-C19A
 with sigma of 0.02
 C19-C20 \\sim C19A-C20A
 with sigma of 0.02
 C19-C21 \\sim C19A-C21A
 with sigma of 0.02
 O4-O3 \\sim O4A-O3A
 with sigma of 0.04
 O4-C20 \\sim O4A-C20A
 with sigma of 0.04
 O4-C21 \\sim O4A-C21A
 with sigma of 0.04
 O3-C20 \\sim O3A-C20A
 with sigma of 0.04
 O3-C21 \\sim O3A-C21A
 with sigma of 0.04
 C18-C19 \\sim C18-C19A
 with sigma of 0.04
 C17-C19 \\sim C17-C19A
 with sigma of 0.04
 C20-C21 \\sim C20A-C21A
 with sigma of 0.04
3. Others
 Sof(O3A)=Sof(O4A)=Sof(C19A)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C21A)=
 Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(1)
 Sof(O3)=Sof(O4)=Sof(C19)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C21)=
 Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8)
4.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F), C21(H21A,H21B,
 H21C), C21A(H21D,H21E,H21F)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 1.07539(18) 0.64609(18) 0.40212(8) 0.0684(6) Uani 1 1 d . . . . .
O2 O 0.86357(13) 0.33638(17) 0.20997(7) 0.0468(4) Uani 1 1 d . . . . .
O3 O 1.02812(16) 0.41065(19) 0.41880(8) 0.0308(6) Uani 0.765(3) 1 d D . P A 1
O3A O 0.9274(5) 0.4926(6) 0.4067(3) 0.0298(18) Uani 0.235(3) 1 d D . P A 2
O4 O 0.9166(2) 0.2585(2) 0.32216(9) 0.0280(5) Uani 0.765(3) 1 d D . P A 1
O4A O 0.8394(7) 0.3078(7) 0.3189(3) 0.0284(16) Uani 0.235(3) 1 d D . P A 2
N1 N 1.00872(15) 0.77359(16) 0.24923(8) 0.0297(4) Uani 1 1 d . . . . .
C1 C 1.05383(16) 0.78382(19) 0.18415(10) 0.0252(4) Uani 1 1 d . . . . .
C2 C 1.05732(16) 0.91916(19) 0.14700(10) 0.0282(4) Uani 1 1 d . . . . .
H2 H 1.033309 1.009940 0.168187 0.034 Uiso 1 1 calc R . . . .
C3 C 1.09507(16) 0.9275(2) 0.07904(10) 0.0286(4) Uani 1 1 d . . . . .
H3 H 1.099874 1.022930 0.056340 0.034 Uiso 1 1 calc R . . . .
C4 C 1.12463(16) 0.7981(2) 0.04603(10) 0.0270(4) Uani 1 1 d . . . . .
C5 C 1.12514(15) 0.66067(19) 0.08427(10) 0.0248(4) Uani 1 1 d . . . . .
C6 C 1.16246(16) 0.5372(2) 0.04548(10) 0.0287(4) Uani 1 1 d . . . . .
C7 C 1.17817(17) 0.3986(2) 0.07813(11) 0.0346(5) Uani 1 1 d . . . . .
H7 H 1.201090 0.312759 0.052832 0.042 Uiso 1 1 calc R . . . .
C8 C 1.15966(17) 0.3853(2) 0.15045(11) 0.0321(5) Uani 1 1 d . . . . .
H8 H 1.174418 0.289441 0.173644 0.039 Uiso 1 1 calc R . . . .
C9 C 1.12157(15) 0.50341(19) 0.18885(10) 0.0261(4) Uani 1 1 d . . . . .
C10 C 1.09784(15) 0.64846(18) 0.15430(9) 0.0235(4) Uani 1 1 d . . . . .
C11 C 1.1640(2) 0.7669(2) -0.02561(11) 0.0355(5) Uani 1 1 d . . . . .
H11A H 1.097(2) 0.801(2) -0.0671(11) 0.047(6) Uiso 1 1 d . . . . .
H11B H 1.246(2) 0.820(2) -0.0288(11) 0.056(7) Uiso 1 1 d . . . . .
C12 C 1.1782(2) 0.5923(2) -0.02846(11) 0.0350(5) Uani 1 1 d . . . . .
H12A H 1.265(2) 0.564(2) -0.0389(10) 0.044(6) Uiso 1 1 d . . . . .
H12B H 1.1097(19) 0.547(2) -0.0689(10) 0.038(5) Uiso 1 1 d . . . . .
C13 C 0.9812(2) 0.9136(2) 0.28410(11) 0.0408(5) Uani 1 1 d . . . . .
H13A H 1.057970 0.979978 0.290487 0.061 Uiso 1 1 calc GR . . . .
H13B H 0.960757 0.890573 0.331655 0.061 Uiso 1 1 calc GR . . . .
H13C H 0.906253 0.964502 0.253656 0.061 Uiso 1 1 calc GR . . . .
C14 C 0.92060(17) 0.6475(2) 0.25414(10) 0.0313(4) Uani 1 1 d . . . . .
H14A H 0.876360 0.617521 0.204492 0.038 Uiso 1 1 calc R . . . .
H14B H 0.852400 0.681495 0.280447 0.038 Uiso 1 1 calc R . . . .
C15 C 1.12465(16) 0.4857(2) 0.26888(10) 0.0300(4) Uani 1 1 d . . . . .
H15A H 1.188158 0.559571 0.295437 0.036 Uiso 1 1 calc R . . . .
H15B H 1.158005 0.383058 0.283758 0.036 Uiso 1 1 calc R . . . .
C16 C 0.99165(17) 0.5077(2) 0.29356(9) 0.0278(4) Uani 1 1 d . . . . .
C17 C 1.02560(19) 0.5352(2) 0.37428(11) 0.0350(5) Uani 1 1 d D . . . .
C18 C 0.91089(17) 0.3669(2) 0.27110(10) 0.0278(4) Uani 1 1 d D . . . .
C19 C 0.9283(4) 0.2991(5) 0.3973(2) 0.0240(9) Uani 0.765(3) 1 d D . P A 1
C19A C 0.8817(12) 0.3392(13) 0.3951(6) 0.020(3) Uani 0.235(3) 1 d D . P A 2
C20 C 0.8002(4) 0.3618(4) 0.4088(2) 0.0332(8) Uani 0.765(3) 1 d D . P A 1
H20A H 0.776961 0.451278 0.378063 0.050 Uiso 0.765(3) 1 calc GR . P A 1
H20B H 0.808096 0.390275 0.459962 0.050 Uiso 0.765(3) 1 calc GR . P A 1
H20C H 0.731791 0.284653 0.396023 0.050 Uiso 0.765(3) 1 calc GR . P A 1
C20A C 0.7651(12) 0.3263(15) 0.4293(7) 0.036(3) Uani 0.235(3) 1 d D . P A 2
H20D H 0.699028 0.400553 0.407285 0.054 Uiso 0.235(3) 1 calc GR . P A 2
H20E H 0.790991 0.346015 0.481555 0.054 Uiso 0.235(3) 1 calc GR . P A 2
H20F H 0.728541 0.223977 0.421518 0.054 Uiso 0.235(3) 1 calc GR . P A 2
C21 C 0.9749(4) 0.1598(4) 0.44041(18) 0.0378(8) Uani 0.765(3) 1 d D . P A 1
H21A H 0.913186 0.076627 0.425174 0.057 Uiso 0.765(3) 1 calc GR . P A 1
H21B H 0.980479 0.180308 0.492219 0.057 Uiso 0.765(3) 1 calc GR . P A 1
H21C H 1.061540 0.131218 0.432050 0.057 Uiso 0.765(3) 1 calc GR . P A 1
C21A C 0.9897(12) 0.2336(14) 0.4254(6) 0.042(3) Uani 0.235(3) 1 d D . P A 2
H21D H 0.958003 0.129000 0.419089 0.063 Uiso 0.235(3) 1 calc GR . P A 2
H21E H 1.020390 0.254640 0.477254 0.063 Uiso 0.235(3) 1 calc GR . P A 2
H21F H 1.062096 0.247588 0.399817 0.063 Uiso 0.235(3) 1 calc GR . P A 2


_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 C17 1.180(2) . ?
O2 C18 1.186(2) . ?
O3 C17 1.378(2) . ?
O3 C19 1.431(4) . ?
O3A C17 1.345(5) . ?
O3A C19A 1.437(11) . ?
O4 C18 1.348(2) . ?
O4 C19 1.436(4) . ?
O4A C18 1.379(5) . ?
O4A C19A 1.438(11) . ?
N1 C1 1.398(2) . ?
N1 C13 1.453(2) . ?
N1 C14 1.457(2) . ?
C1 C2 1.387(2) . ?
C1 C10 1.433(2) . ?
C2 C3 1.411(3) . ?
C3 C4 1.363(2) . ?
C4 C5 1.409(2) . ?
C4 C11 1.509(3) . ?
C5 C6 1.408(2) . ?
C5 C10 1.404(2) . ?
C6 C7 1.363(3) . ?
C6 C12 1.511(3) . ?
C7 C8 1.415(3) . ?
C8 C9 1.370(2) . ?
C9 C10 1.434(2) . ?
C9 C15 1.505(2) . ?
C11 C12 1.550(3) . ?
C14 C16 1.549(2) . ?
C15 C16 1.560(2) . ?
C16 C17 1.506(3) . ?
C16 C18 1.512(2) . ?
C19 C20 1.502(5) . ?
C19 C21 1.499(4) . ?
C19A C20A 1.488(11) . ?
C19A C21A 1.484(11) . ?

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
C17 O3 C19 116.9(2) . . ?
C17 O3A C19A 117.0(6) . . ?
C18 O4 C19 120.3(2) . . ?
C18 O4A C19A 118.5(6) . . ?
C1 N1 C13 118.07(15) . . ?
C1 N1 C14 115.56(14) . . ?
C13 N1 C14 115.87(15) . . ?
N1 C1 C10 118.57(15) . . ?
C2 C1 N1 122.86(16) . . ?
C2 C1 C10 118.56(17) . . ?
C1 C2 C3 122.67(17) . . ?
C4 C3 C2 119.83(16) . . ?
C3 C4 C5 117.85(17) . . ?
C3 C4 C11 133.25(17) . . ?
C5 C4 C11 108.86(16) . . ?
C6 C5 C4 112.07(17) . . ?
C10 C5 C4 124.22(16) . . ?
C10 C5 C6 123.64(16) . . ?
C5 C6 C12 108.57(16) . . ?
C7 C6 C5 118.83(18) . . ?
C7 C6 C12 132.59(18) . . ?
C6 C7 C8 118.63(18) . . ?
C9 C8 C7 123.48(17) . . ?
C8 C9 C10 118.85(17) . . ?
C8 C9 C15 119.73(16) . . ?
C10 C9 C15 120.79(16) . . ?
C1 C10 C9 127.35(17) . . ?
C5 C10 C1 116.30(15) . . ?
C5 C10 C9 116.31(16) . . ?
C4 C11 C12 104.90(16) . . ?
C6 C12 C11 105.05(16) . . ?
N1 C14 C16 113.02(14) . . ?
C9 C15 C16 116.19(14) . . ?
C14 C16 C15 109.01(14) . . ?
C17 C16 C14 110.26(15) . . ?
C17 C16 C15 105.99(14) . . ?
C17 C16 C18 114.75(15) . . ?
C18 C16 C14 109.54(14) . . ?
C18 C16 C15 107.05(15) . . ?
O1 C17 O3 116.06(18) . . ?
O1 C17 O3A 109.8(3) . . ?
O1 C17 C16 125.01(18) . . ?
O3 C17 C16 117.03(16) . . ?
O3A C17 C16 111.3(3) . . ?
O2 C18 O4 118.55(17) . . ?
O2 C18 O4A 111.7(3) . . ?
O2 C18 C16 123.85(17) . . ?
O4 C18 C16 116.22(15) . . ?
O4A C18 C16 118.2(3) . . ?
O3 C19 O4 111.3(3) . . ?
O3 C19 C20 108.9(3) . . ?
O3 C19 C21 105.8(3) . . ?
O4 C19 C20 109.3(3) . . ?
O4 C19 C21 106.3(3) . . ?
C21 C19 C20 115.2(3) . . ?
O3A C19A O4A 111.0(8) . . ?
O3A C19A C20A 106.4(9) . . ?
O3A C19A C21A 109.3(10) . . ?
O4A C19A C20A 107.5(9) . . ?
O4A C19A C21A 108.5(9) . . ?
C21A C19A C20A 114.2(10) . . ?

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 -175.87(15) . . . . ?
N1 C1 C10 C5 171.57(14) . . . . ?
N1 C1 C10 C9 -10.8(2) . . . . ?
N1 C14 C16 C15 -40.6(2) . . . . ?
N1 C14 C16 C17 75.32(19) . . . . ?
N1 C14 C16 C18 -157.48(15) . . . . ?
C1 N1 C14 C16 96.10(18) . . . . ?
C1 C2 C3 C4 2.8(3) . . . . ?
C2 C1 C10 C5 -8.1(2) . . . . ?
C2 C1 C10 C9 169.45(15) . . . . ?
C2 C3 C4 C5 -4.5(2) . . . . ?
C2 C3 C4 C11 178.20(18) . . . . ?
C3 C4 C5 C6 -177.50(15) . . . . ?
C3 C4 C5 C10 -0.3(3) . . . . ?
C3 C4 C11 C12 -178.36(19) . . . . ?
C4 C5 C6 C7 174.56(15) . . . . ?
C4 C5 C6 C12 -5.0(2) . . . . ?
C4 C5 C10 C1 6.7(2) . . . . ?
C4 C5 C10 C9 -171.17(15) . . . . ?
C4 C11 C12 C6 -6.8(2) . . . . ?
C5 C4 C11 C12 4.1(2) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
C5 C6 C12 C11 7.3(2) . . . . ?
C6 C5 C10 C1 -176.48(15) . . . . ?
C6 C5 C10 C9 5.7(2) . . . . ?
C6 C7 C8 C9 2.7(3) . . . . ?
C7 C6 C12 C11 -172.21(19) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C7 C8 C9 C15 -170.45(16) . . . . ?
C8 C9 C10 C1 177.93(16) . . . . ?
C8 C9 C10 C5 -4.5(2) . . . . ?
C8 C9 C15 C16 -120.95(18) . . . . ?
C9 C15 C16 C14 -43.4(2) . . . . ?
C9 C15 C16 C17 -162.08(15) . . . . ?
C9 C15 C16 C18 75.00(18) . . . . ?
C10 C1 C2 C3 3.8(2) . . . . ?
C10 C5 C6 C7 -2.6(3) . . . . ?
C10 C5 C6 C12 177.79(15) . . . . ?
C10 C9 C15 C16 68.2(2) . . . . ?
C11 C4 C5 C6 0.4(2) . . . . ?
C11 C4 C5 C10 177.60(16) . . . . ?
C12 C6 C7 C8 177.85(18) . . . . ?
C13 N1 C1 C2 -8.5(2) . . . . ?
C13 N1 C1 C10 171.80(16) . . . . ?
C13 N1 C14 C16 -119.65(17) . . . . ?
C14 N1 C1 C2 134.93(17) . . . . ?
C14 N1 C1 C10 -44.8(2) . . . . ?
C14 C16 C17 O1 -47.2(3) . . . . ?
C14 C16 C17 O3 149.10(16) . . . . ?
C14 C16 C17 O3A 88.6(3) . . . . ?
C14 C16 C18 O2 47.0(2) . . . . ?
C14 C16 C18 O4 -146.68(17) . . . . ?
C14 C16 C18 O4A -102.9(4) . . . . ?
C15 C9 C10 C1 -11.2(3) . . . . ?
C15 C9 C10 C5 166.42(15) . . . . ?
C15 C16 C17 O1 70.6(3) . . . . ?
C15 C16 C17 O3 -93.06(19) . . . . ?
C15 C16 C17 O3A -153.6(3) . . . . ?
C15 C16 C18 O2 -71.1(2) . . . . ?
C15 C16 C18 O4 95.3(2) . . . . ?
C15 C16 C18 O4A 139.0(4) . . . . ?
C17 O3 C19 O4 48.6(4) . . . . ?
C17 O3 C19 C20 -71.9(3) . . . . ?
C17 O3 C19 C21 163.7(2) . . . . ?
C17 O3A C19A O4A -57.2(10) . . . . ?
C17 O3A C19A C20A -173.8(7) . . . . ?
C17 O3A C19A C21A 62.4(10) . . . . ?
C17 C16 C18 O2 171.59(18) . . . . ?
C17 C16 C18 O4 -22.0(2) . . . . ?
C17 C16 C18 O4A 21.7(4) . . . . ?
C18 O4 C19 O3 -47.3(4) . . . . ?
C18 O4 C19 C20 73.0(3) . . . . ?
C18 O4 C19 C21 -162.1(3) . . . . ?
C18 O4A C19A O3A 39.3(11) . . . . ?
C18 O4A C19A C20A 155.2(8) . . . . ?
C18 O4A C19A C21A -80.8(11) . . . . ?
C18 C16 C17 O1 -171.5(2) . . . . ?
C18 C16 C17 O3 24.8(2) . . . . ?
C18 C16 C17 O3A -35.7(3) . . . . ?
C19 O3 C17 O1 155.3(3) . . . . ?
C19 O3 C17 C16 -39.5(3) . . . . ?
C19 O4 C18 O2 -158.0(2) . . . . ?
C19 O4 C18 C16 34.9(3) . . . . ?
C19A O3A C17 O1 -162.1(6) . . . . ?
C19A O3A C17 C16 55.2(7) . . . . ?
C19A O4A C18 O2 -178.0(7) . . . . ?
C19A O4A C18 C16 -24.6(9) . . . . ?

_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 1.034
_oxdiff_exptl_absorpt_empirical_full_min 0.971
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/hexane'
####################################################################### 
# 
# 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_jb425abs
_database_code_depnum_ccdc_archive 'CCDC 2069091'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 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        
;
methyl (E)-2-cyano-3-(6-(dimethylamino)-1,2-dihydroacenaphthylen-5-yl)propenoate, 
;
_chemical_formula_moiety         'C19 H18 N2 O2'
_chemical_formula_sum            'C19 H18 N2 O2'
_chemical_formula_weight         306.35
_chemical_melting_point          355-358
_chemical_oxdiff_formula         'C19 H18 N2 O2'
_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'
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                   8.7457(5)
_cell_length_b                   9.3638(7)
_cell_length_c                   11.2739(7)
_cell_angle_alpha                108.887(6)
_cell_angle_beta                 91.171(5)
_cell_angle_gamma                113.671(6)
_cell_volume                     787.91(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2776
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      30.2620
_cell_measurement_theta_min      3.6010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.887
_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    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             324
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 15 0.0960
-1 2 -15 0.1016
0 -12 7 0.1805
0 12 -6 0.3023
-11 0 3 0.1921
-10 11 -1 0.1551
4 -13 3 0.1534
10 0 -9 0.1254

_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.371
_exptl_crystal_size_min          0.226
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
1.0000 -0.0000 15.0000 0.5056 0.8826 0.1755
-1.0000 2.0000 -15.0000 -0.4837 -0.8479 -0.0028
0.0000 -12.0000 7.0000 0.1325 0.1781 -0.9712
-0.0000 12.0000 -6.0000 -0.0947 -0.1229 0.9805
-11.0000 -0.0000 3.0000 0.7859 -0.4373 -0.3754
-10.0000 11.0000 -1.0000 0.6946 -0.4124 0.5739
4.0000 -13.0000 3.0000 -0.2742 0.1593 -0.9480
10.0000 0.0000 -9.0000 -0.9515 0.0514 0.2832

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7276
_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         3.489
_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 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  88.00   1.00    7.50    --   20.20  77.00 150.00   95
  2  ω    -47.00  47.00   1.00    7.50    --   20.20 -77.00 -60.00   94
  3  ω    -47.00  -5.00   1.00    7.50    --   20.20 -77.00  30.00   42
  4  ω     -7.00  87.00   1.00    7.50    --   20.20  77.00  60.00   94
  5  ω    -18.00  57.00   1.00    7.50    --   20.20 -99.00 -90.00   75
;
_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      -0.0611398000
_diffrn_orient_matrix_UB_12      0.0109973000
_diffrn_orient_matrix_UB_13      0.0377857000
_diffrn_orient_matrix_UB_21      0.0548096000
_diffrn_orient_matrix_UB_22      0.0173495000
_diffrn_orient_matrix_UB_23      0.0551865000
_diffrn_orient_matrix_UB_31      0.0366483000
_diffrn_orient_matrix_UB_32      0.0863327000
_diffrn_orient_matrix_UB_33      0.0092538000
_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                2990
_reflns_number_total             3915
_reflns_odcompleteness_completeness 99.82
_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         0.304
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3915
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+0.1400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1360
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C15(H15)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_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 0.12950(14) 0.91260(14) 0.07881(11) 0.0390(3) Uani 1 1 d . . . . .
O2 O -0.10701(13) 0.67029(13) 0.00438(10) 0.0328(3) Uani 1 1 d . . . . .
N1 N 0.55248(16) 0.86997(17) 0.19540(12) 0.0336(3) Uani 1 1 d . . . . .
N2 N -0.15364(17) 0.43611(18) 0.18267(13) 0.0409(4) Uani 1 1 d . . . . .
C1 C 0.59320(18) 0.84320(19) 0.30720(15) 0.0306(3) Uani 1 1 d . . . . .
C2 C 0.7552(2) 0.8675(2) 0.34784(17) 0.0396(4) Uani 1 1 d . . . . .
H2 H 0.839565 0.905714 0.301837 0.048 Uiso 1 1 calc R . . . .
C3 C 0.7989(2) 0.8372(2) 0.45540(18) 0.0426(4) Uani 1 1 d . . . . .
H3 H 0.909710 0.856016 0.479450 0.051 Uiso 1 1 calc R . . . .
C4 C 0.67799(19) 0.7804(2) 0.52335(16) 0.0351(4) Uani 1 1 d . . . . .
C5 C 0.51217(18) 0.75662(18) 0.48485(14) 0.0284(3) Uani 1 1 d . . . . .
C6 C 0.4018(2) 0.69770(19) 0.56512(14) 0.0317(3) Uani 1 1 d . . . . .
C7 C 0.2352(2) 0.6650(2) 0.53980(15) 0.0334(3) Uani 1 1 d . . . . .
H7 H 0.158943 0.622521 0.589554 0.040 Uiso 1 1 calc R . . . .
C8 C 0.18190(18) 0.69726(19) 0.43677(15) 0.0308(3) Uani 1 1 d . . . . .
H8 H 0.068630 0.675939 0.420483 0.037 Uiso 1 1 calc R . . . .
C9 C 0.28845(17) 0.75906(18) 0.35788(14) 0.0267(3) Uani 1 1 d . . . . .
C10 C 0.46330(17) 0.78846(17) 0.37954(13) 0.0258(3) Uani 1 1 d . . . . .
C11 C 0.4696(2) 0.7142(2) 0.08584(16) 0.0432(4) Uani 1 1 d . . . . .
H11A H 0.548756 0.667413 0.060992 0.065 Uiso 1 1 calc GR . . . .
H11B H 0.430548 0.736108 0.016384 0.065 Uiso 1 1 calc GR . . . .
H11C H 0.374825 0.636369 0.108047 0.065 Uiso 1 1 calc GR . . . .
C12 C 0.6920(2) 0.9921(2) 0.16068(18) 0.0450(4) Uani 1 1 d . . . . .
H12A H 0.746739 1.093966 0.233353 0.067 Uiso 1 1 calc GR . . . .
H12B H 0.648464 1.014392 0.093233 0.067 Uiso 1 1 calc GR . . . .
H12C H 0.772434 0.948109 0.132663 0.067 Uiso 1 1 calc GR . . . .
C13 C 0.6818(2) 0.7332(2) 0.63918(16) 0.0419(4) Uani 1 1 d . . . . .
H13A H 0.763282 0.827154 0.710246 0.050 Uiso 1 1 calc R . . . .
H13B H 0.711762 0.640117 0.621114 0.050 Uiso 1 1 calc R . . . .
C14 C 0.5005(2) 0.6835(2) 0.66936(17) 0.0428(4) Uani 1 1 d . . . . .
H14A H 0.451626 0.570013 0.668450 0.051 Uiso 1 1 calc R . . . .
H14B H 0.500669 0.758551 0.752271 0.051 Uiso 1 1 calc R . . . .
C15 C 0.22416(18) 0.80134(19) 0.25944(14) 0.0281(3) Uani 1 1 d . . . . .
H15 H 0.297513 0.898849 0.248639 0.034 Uiso 1 1 calc R . . . .
C16 C 0.07264(18) 0.71685(19) 0.18297(14) 0.0277(3) Uani 1 1 d . . . . .
C17 C -0.05391(18) 0.56054(19) 0.18296(14) 0.0293(3) Uani 1 1 d . . . . .
C18 C 0.03745(18) 0.78010(19) 0.08497(14) 0.0279(3) Uani 1 1 d . . . . .
C19 C -0.1447(2) 0.7155(2) -0.10049(16) 0.0375(4) Uani 1 1 d . . . . .
H19A H -0.058276 0.721776 -0.152410 0.056 Uiso 1 1 calc GR . . . .
H19B H -0.147986 0.822287 -0.067531 0.056 Uiso 1 1 calc GR . . . .
H19C H -0.252613 0.632447 -0.150886 0.056 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 C18 1.2034(17) . ?
O2 C18 1.3357(18) . ?
O2 C19 1.4511(16) . ?
N1 C1 1.4269(19) . ?
N1 C11 1.459(2) . ?
N1 C12 1.4625(19) . ?
N2 C17 1.1401(19) . ?
C1 C2 1.385(2) . ?
C1 C10 1.435(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.410(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.354(2) . ?
C4 C5 1.412(2) . ?
C4 C13 1.512(2) . ?
C5 C6 1.409(2) . ?
C5 C10 1.4113(18) . ?
C6 C7 1.366(2) . ?
C6 C14 1.515(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.405(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.389(2) . ?
C9 C10 1.4412(19) . ?
C9 C15 1.4637(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 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.542(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15 0.9300 . ?
C15 C16 1.340(2) . ?
C16 C17 1.437(2) . ?
C16 C18 1.4908(18) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O2 C19 115.29(11) . . ?
C1 N1 C11 112.33(12) . . ?
C1 N1 C12 115.94(13) . . ?
C11 N1 C12 109.86(13) . . ?
N1 C1 C10 119.53(12) . . ?
C2 C1 N1 121.76(13) . . ?
C2 C1 C10 118.70(14) . . ?
C1 C2 H2 118.3 . . ?
C1 C2 C3 123.35(15) . . ?
C3 C2 H2 118.3 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.37(14) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 118.41(15) . . ?
C3 C4 C13 132.46(14) . . ?
C5 C4 C13 109.12(14) . . ?
C6 C5 C4 111.47(13) . . ?
C6 C5 C10 124.29(13) . . ?
C10 C5 C4 124.24(14) . . ?
C5 C6 C14 109.14(13) . . ?
C7 C6 C5 119.05(13) . . ?
C7 C6 C14 131.80(14) . . ?
C6 C7 H7 120.8 . . ?
C6 C7 C8 118.41(13) . . ?
C8 C7 H7 120.8 . . ?
C7 C8 H8 118.1 . . ?
C9 C8 C7 123.83(13) . . ?
C9 C8 H8 118.1 . . ?
C8 C9 C10 118.85(12) . . ?
C8 C9 C15 119.72(12) . . ?
C10 C9 C15 121.36(12) . . ?
C1 C10 C9 128.62(13) . . ?
C5 C10 C1 115.87(12) . . ?
C5 C10 C9 115.50(12) . . ?
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 . . ?
C4 C13 H13A 110.7 . . ?
C4 C13 H13B 110.7 . . ?
C4 C13 C14 105.16(12) . . ?
H13A C13 H13B 108.8 . . ?
C14 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
C6 C14 C13 105.04(13) . . ?
C6 C14 H14A 110.7 . . ?
C6 C14 H14B 110.7 . . ?
C13 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C9 C15 H15 116.0 . . ?
C16 C15 C9 127.99(13) . . ?
C16 C15 H15 116.0 . . ?
C15 C16 C17 123.63(12) . . ?
C15 C16 C18 118.60(13) . . ?
C17 C16 C18 117.58(13) . . ?
N2 C17 C16 179.58(19) . . ?
O1 C18 O2 124.62(12) . . ?
O1 C18 C16 123.89(14) . . ?
O2 C18 C16 111.48(12) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -177.91(16) . . . . ?
N1 C1 C10 C5 176.81(13) . . . . ?
N1 C1 C10 C9 -2.1(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C1 C10 C5 -2.7(2) . . . . ?
C2 C1 C10 C9 178.33(15) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C2 C3 C4 C13 178.57(17) . . . . ?
C3 C4 C5 C6 -179.88(15) . . . . ?
C3 C4 C5 C10 -0.1(2) . . . . ?
C3 C4 C13 C14 178.38(19) . . . . ?
C4 C5 C6 C7 -178.82(14) . . . . ?
C4 C5 C6 C14 1.42(19) . . . . ?
C4 C5 C10 C1 2.1(2) . . . . ?
C4 C5 C10 C9 -178.83(14) . . . . ?
C4 C13 C14 C6 2.57(18) . . . . ?
C5 C4 C13 C14 -1.85(18) . . . . ?
C5 C6 C7 C8 -2.2(2) . . . . ?
C5 C6 C14 C13 -2.49(18) . . . . ?
C6 C5 C10 C1 -178.18(14) . . . . ?
C6 C5 C10 C9 0.9(2) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
C7 C6 C14 C13 177.80(17) . . . . ?
C7 C8 C9 C10 1.7(2) . . . . ?
C7 C8 C9 C15 -175.05(15) . . . . ?
C8 C9 C10 C1 176.58(15) . . . . ?
C8 C9 C10 C5 -2.4(2) . . . . ?
C8 C9 C15 C16 -40.8(2) . . . . ?
C9 C15 C16 C17 -2.5(3) . . . . ?
C9 C15 C16 C18 -177.30(14) . . . . ?
C10 C1 C2 C3 1.6(3) . . . . ?
C10 C5 C6 C7 1.4(2) . . . . ?
C10 C5 C6 C14 -178.34(14) . . . . ?
C10 C9 C15 C16 142.51(16) . . . . ?
C11 N1 C1 C2 99.97(18) . . . . ?
C11 N1 C1 C10 -79.56(17) . . . . ?
C12 N1 C1 C2 -27.5(2) . . . . ?
C12 N1 C1 C10 152.97(14) . . . . ?
C13 C4 C5 C6 0.31(19) . . . . ?
C13 C4 C5 C10 -179.93(14) . . . . ?
C14 C6 C7 C8 177.51(16) . . . . ?
C15 C9 C10 C1 -6.7(2) . . . . ?
C15 C9 C10 C5 174.33(13) . . . . ?
C15 C16 C18 O1 -8.4(2) . . . . ?
C15 C16 C18 O2 170.59(14) . . . . ?
C17 C16 C18 O1 176.43(15) . . . . ?
C17 C16 C18 O2 -4.55(18) . . . . ?
C19 O2 C18 O1 3.7(2) . . . . ?
C19 O2 C18 C16 -175.27(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 1.734
_oxdiff_exptl_absorpt_empirical_full_min 0.900
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/hexane'
####################################################################### 
# 
# 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_jb290absbeam
_database_code_depnum_ccdc_archive 'CCDC 2069098'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 downloaded from the CCDC.
;
_audit_creation_date             2019-09-17
_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_systematic        
1,2,2,8,8-Pentamethyl-1,2,3,4-tetrahydro-8H-spiro[1,3-dioxane-5,3-fluoreno[4,5-bcd]azocine]-4,6-dione
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H25 N O4'
_chemical_formula_sum            'C24 H25 N O4'
_chemical_formula_weight         391.45
_chemical_melting_point          477-480
_chemical_oxdiff_formula         'C24 O4 N1 H26'
_chemical_oxdiff_usercomment     'Colourless 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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9539(3)
_cell_length_b                   9.5493(3)
_cell_length_c                   19.3902(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.652(3)
_cell_angle_gamma                90
_cell_volume                     1962.30(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3805
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.2120
_cell_measurement_theta_min      2.4320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.916
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-10 8 -9 0.0968
8 -11 1 0.0975
10 -5 13 0.0914
0 -9 -19 0.0733
-12 -4 21 0.0625
12 4 -20 0.1033
1 11 15 0.0987
10 -8 9 0.0968

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/hexane'
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.169
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
-10.0114 8.0373 -9.1424 0.4688 -0.9052 -0.0355
8.0141 -11.0415 1.1036 -0.3983 0.7894 0.4380
10.0081 -5.0297 13.1490 -0.4524 0.8624 -0.2306
0.0200 -9.0211 -19.0500 0.1450 0.0726 0.9702
-12.0723 -4.0027 21.0151 -0.8962 -0.4921 -0.0629
12.0709 4.0025 -20.0108 0.8685 0.5001 0.0383
0.9908 11.0267 15.0331 0.0628 -0.0912 -1.0029
10.0114 -8.0373 9.1424 -0.4688 0.9052 0.0355

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9504
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.262
_diffrn_reflns_theta_min         2.171
_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 1.000
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  42.00   1.00   75.00    --  -16.00  19.00  60.00   42
  2  ω    -43.00  21.00   1.00   75.00    --   16.16 -57.00 -30.00   64
  3  ω     -1.00  72.00   1.00   75.00    --   16.16  57.00 150.00   73
  4  ω     26.00  71.00   1.00   75.00    --   16.16  57.00 -90.00   45
;
_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      0.0122350000
_diffrn_orient_matrix_UB_12      0.0421938000
_diffrn_orient_matrix_UB_13      -0.0275799000
_diffrn_orient_matrix_UB_21      0.0630533000
_diffrn_orient_matrix_UB_22      -0.0249218000
_diffrn_orient_matrix_UB_23      0.0080591000
_diffrn_orient_matrix_UB_31      -0.0189211000
_diffrn_orient_matrix_UB_32      -0.0558525000
_diffrn_orient_matrix_UB_33      -0.0244987000
_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                3645
_reflns_number_total             4532
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (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         0.276
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.057
_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)+(0.0408P)²+0.6605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1109
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C)
;
_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
O1 O 0.58407(10) 0.44791(12) 0.56899(6) 0.0230(3) Uani 1 1 d . . . . .
O2 O 0.37201(11) 0.72337(12) 0.70498(6) 0.0264(3) Uani 1 1 d . . . . .
O3 O 0.40543(10) 0.38594(12) 0.59212(7) 0.0264(3) Uani 1 1 d . . . . .
O4 O 0.28635(10) 0.53863(12) 0.64567(6) 0.0231(3) Uani 1 1 d . . . . .
N1 N 0.52560(12) 0.87755(14) 0.61246(7) 0.0195(3) Uani 1 1 d . . . . .
C1 C 0.64042(14) 0.94502(17) 0.61426(8) 0.0173(3) Uani 1 1 d . . . . .
C2 C 0.64294(15) 1.09037(17) 0.60231(9) 0.0215(4) Uani 1 1 d . . . . .
H2 H 0.568724 1.141428 0.596512 0.026 Uiso 1 1 calc R . . . .
C3 C 0.75244(16) 1.15983(18) 0.59892(9) 0.0241(4) Uani 1 1 d . . . . .
H3 H 0.750838 1.256324 0.592278 0.029 Uiso 1 1 calc R . . . .
C4 C 0.86443(15) 1.08698(17) 0.60532(9) 0.0220(4) Uani 1 1 d . . . . .
H4 H 0.936626 1.132308 0.599977 0.026 Uiso 1 1 calc R . . . .
C5 C 0.86565(14) 0.94501(17) 0.61987(8) 0.0176(3) Uani 1 1 d . . . . .
C6 C 0.75795(14) 0.87307(16) 0.62813(8) 0.0160(3) Uani 1 1 d . . . . .
C7 C 0.79857(14) 0.72833(16) 0.65311(8) 0.0157(3) Uani 1 1 d . . . . .
C8 C 0.73980(14) 0.61824(16) 0.68097(8) 0.0161(3) Uani 1 1 d . . . . .
C9 C 0.80829(15) 0.49467(17) 0.70071(8) 0.0201(3) Uani 1 1 d . . . . .
H9 H 0.769337 0.419948 0.717348 0.024 Uiso 1 1 calc R . . . .
C10 C 0.93193(15) 0.47933(18) 0.69643(9) 0.0232(4) Uani 1 1 d . . . . .
H10 H 0.973894 0.394817 0.708920 0.028 Uiso 1 1 calc R . . . .
C11 C 0.99303(15) 0.59099(17) 0.67334(9) 0.0213(4) Uani 1 1 d . . . . .
H11 H 1.077072 0.583344 0.672074 0.026 Uiso 1 1 calc R . . . .
C12 C 0.92669(14) 0.71355(17) 0.65231(8) 0.0167(3) Uani 1 1 d . . . . .
C13 C 0.98031(14) 0.84980(16) 0.63272(8) 0.0181(3) Uani 1 1 d . . . . .
C14 C 1.03152(16) 0.83648(19) 0.56623(9) 0.0255(4) Uani 1 1 d . . . . .
H14A H 1.099448 0.769981 0.575214 0.038 Uiso 1 1 calc GR . . . .
H14B H 1.061822 0.925946 0.555213 0.038 Uiso 1 1 calc GR . . . .
H14C H 0.965307 0.805180 0.526703 0.038 Uiso 1 1 calc GR . . . .
C15 C 1.08597(15) 0.90216(19) 0.69555(9) 0.0258(4) Uani 1 1 d . . . . .
H15A H 1.056320 0.903001 0.738096 0.039 Uiso 1 1 calc GR . . . .
H15B H 1.110083 0.995219 0.685691 0.039 Uiso 1 1 calc GR . . . .
H15C H 1.157538 0.840972 0.702131 0.039 Uiso 1 1 calc GR . . . .
C16 C 0.41299(15) 0.96533(18) 0.60375(10) 0.0274(4) Uani 1 1 d . . . . .
H16A H 0.427373 1.034489 0.640863 0.041 Uiso 1 1 calc GR . . . .
H16B H 0.342397 0.907940 0.606463 0.041 Uiso 1 1 calc GR . . . .
H16C H 0.395414 1.011065 0.558204 0.041 Uiso 1 1 calc GR . . . .
C17 C 0.50292(15) 0.74062(16) 0.57881(8) 0.0181(3) Uani 1 1 d . . . . .
H17A H 0.570334 0.719989 0.556162 0.022 Uiso 1 1 calc R . . . .
H17B H 0.424581 0.743812 0.541788 0.022 Uiso 1 1 calc R . . . .
C18 C 0.49484(14) 0.61934(16) 0.63174(8) 0.0162(3) Uani 1 1 d . . . . .
C19 C 0.61218(13) 0.62991(17) 0.69689(8) 0.0161(3) Uani 1 1 d . . . . .
H19A H 0.608403 0.718940 0.720345 0.019 Uiso 1 1 calc R . . . .
H19B H 0.605774 0.556694 0.730473 0.019 Uiso 1 1 calc R . . . .
C20 C 0.49853(14) 0.48061(16) 0.59368(8) 0.0173(3) Uani 1 1 d . . . . .
C21 C 0.38046(14) 0.63392(17) 0.66291(8) 0.0179(3) Uani 1 1 d . . . . .
C22 C 0.28070(15) 0.43205(18) 0.59213(9) 0.0224(4) Uani 1 1 d . . . . .
C23 C 0.21594(18) 0.3076(2) 0.61529(10) 0.0333(4) Uani 1 1 d . . . . .
H23A H 0.214295 0.231418 0.582763 0.050 Uiso 1 1 calc GR . . . .
H23B H 0.131126 0.332596 0.615460 0.050 Uiso 1 1 calc GR . . . .
H23C H 0.261200 0.279639 0.662372 0.050 Uiso 1 1 calc GR . . . .
C24 C 0.21392(16) 0.4901(2) 0.52015(9) 0.0301(4) Uani 1 1 d . . . . .
H24A H 0.258829 0.570510 0.509795 0.045 Uiso 1 1 calc GR . . . .
H24B H 0.129616 0.516899 0.520523 0.045 Uiso 1 1 calc GR . . . .
H24C H 0.210802 0.419911 0.484310 0.045 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 C20 1.1964(18) . ?
O2 C21 1.2007(19) . ?
O3 C20 1.3574(19) . ?
O3 C22 1.4355(19) . ?
O4 C21 1.3520(19) . ?
O4 C22 1.4439(19) . ?
N1 C1 1.406(2) . ?
N1 C16 1.465(2) . ?
N1 C17 1.454(2) . ?
C1 C2 1.409(2) . ?
C1 C6 1.424(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(2) . ?
C5 C6 1.409(2) . ?
C5 C13 1.519(2) . ?
C6 C7 1.495(2) . ?
C7 C8 1.410(2) . ?
C7 C12 1.415(2) . ?
C8 C9 1.399(2) . ?
C8 C19 1.510(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.392(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(2) . ?
C12 C13 1.515(2) . ?
C13 C14 1.536(2) . ?
C13 C15 1.536(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.565(2) . ?
C18 C19 1.561(2) . ?
C18 C20 1.522(2) . ?
C18 C21 1.529(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C22 C23 1.509(2) . ?
C22 C24 1.508(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C20 O3 C22 120.36(12) . . ?
C21 O4 C22 122.92(12) . . ?
C1 N1 C16 117.55(13) . . ?
C1 N1 C17 118.26(13) . . ?
C17 N1 C16 114.79(13) . . ?
N1 C1 C2 120.14(14) . . ?
N1 C1 C6 122.97(14) . . ?
C2 C1 C6 116.89(14) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 C1 122.15(15) . . ?
C3 C2 H2 118.9 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.77(16) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.15(15) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 C6 122.38(14) . . ?
C4 C5 C13 125.78(14) . . ?
C6 C5 C13 111.76(14) . . ?
C1 C6 C7 133.50(14) . . ?
C5 C6 C1 119.10(14) . . ?
C5 C6 C7 107.37(13) . . ?
C8 C7 C6 133.35(14) . . ?
C8 C7 C12 118.71(14) . . ?
C12 C7 C6 107.67(13) . . ?
C7 C8 C19 124.02(14) . . ?
C9 C8 C7 117.95(14) . . ?
C9 C8 C19 117.80(14) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 C8 122.52(15) . . ?
C10 C9 H9 118.7 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.68(15) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 118.92(15) . . ?
C12 C11 H11 120.5 . . ?
C7 C12 C13 111.46(13) . . ?
C11 C12 C7 121.98(14) . . ?
C11 C12 C13 126.33(14) . . ?
C5 C13 C14 111.97(13) . . ?
C5 C13 C15 111.16(13) . . ?
C12 C13 C5 101.44(12) . . ?
C12 C13 C14 112.73(13) . . ?
C12 C13 C15 110.05(13) . . ?
C14 C13 C15 109.31(13) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 108.8 . . ?
N1 C17 H17B 108.8 . . ?
N1 C17 C18 113.75(13) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C19 C18 C17 108.14(12) . . ?
C20 C18 C17 108.25(12) . . ?
C20 C18 C19 109.35(12) . . ?
C20 C18 C21 113.32(13) . . ?
C21 C18 C17 112.32(12) . . ?
C21 C18 C19 105.28(12) . . ?
C8 C19 C18 116.44(12) . . ?
C8 C19 H19A 108.2 . . ?
C8 C19 H19B 108.2 . . ?
C18 C19 H19A 108.2 . . ?
C18 C19 H19B 108.2 . . ?
H19A C19 H19B 107.3 . . ?
O1 C20 O3 118.50(14) . . ?
O1 C20 C18 122.73(14) . . ?
O3 C20 C18 118.59(13) . . ?
O2 C21 O4 117.50(14) . . ?
O2 C21 C18 123.03(14) . . ?
O4 C21 C18 119.39(13) . . ?
O3 C22 O4 110.41(12) . . ?
O3 C22 C23 106.11(14) . . ?
O3 C22 C24 110.58(13) . . ?
O4 C22 C23 106.20(13) . . ?
O4 C22 C24 109.20(14) . . ?
C24 C22 C23 114.23(14) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 -175.66(15) . . . . ?
N1 C1 C6 C5 171.86(14) . . . . ?
N1 C1 C6 C7 -10.0(3) . . . . ?
N1 C17 C18 C19 -50.03(16) . . . . ?
N1 C17 C18 C20 -168.39(12) . . . . ?
N1 C17 C18 C21 65.72(16) . . . . ?
C1 N1 C17 C18 114.23(15) . . . . ?
C1 C2 C3 C4 1.8(3) . . . . ?
C1 C6 C7 C8 -10.3(3) . . . . ?
C1 C6 C7 C12 176.04(16) . . . . ?
C2 C1 C6 C5 -8.4(2) . . . . ?
C2 C1 C6 C7 169.74(16) . . . . ?
C2 C3 C4 C5 -4.2(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C3 C4 C5 C13 -176.44(15) . . . . ?
C4 C5 C6 C1 6.3(2) . . . . ?
C4 C5 C6 C7 -172.27(14) . . . . ?
C4 C5 C13 C12 174.89(15) . . . . ?
C4 C5 C13 C14 -64.7(2) . . . . ?
C4 C5 C13 C15 57.9(2) . . . . ?
C5 C6 C7 C8 168.02(16) . . . . ?
C5 C6 C7 C12 -5.68(16) . . . . ?
C6 C1 C2 C3 4.6(2) . . . . ?
C6 C5 C13 C12 -1.99(16) . . . . ?
C6 C5 C13 C14 118.46(15) . . . . ?
C6 C5 C13 C15 -118.95(15) . . . . ?
C6 C7 C8 C9 -178.65(15) . . . . ?
C6 C7 C8 C19 -4.3(3) . . . . ?
C6 C7 C12 C11 179.36(14) . . . . ?
C6 C7 C12 C13 4.56(17) . . . . ?
C7 C8 C9 C10 2.6(2) . . . . ?
C7 C8 C19 C18 78.45(19) . . . . ?
C7 C12 C13 C5 -1.72(16) . . . . ?
C7 C12 C13 C14 -121.64(14) . . . . ?
C7 C12 C13 C15 116.05(14) . . . . ?
C8 C7 C12 C11 4.6(2) . . . . ?
C8 C7 C12 C13 -170.22(13) . . . . ?
C8 C9 C10 C11 1.6(3) . . . . ?
C9 C8 C19 C18 -107.19(16) . . . . ?
C9 C10 C11 C12 -2.6(2) . . . . ?
C10 C11 C12 C7 -0.4(2) . . . . ?
C10 C11 C12 C13 173.55(15) . . . . ?
C11 C12 C13 C5 -176.25(15) . . . . ?
C11 C12 C13 C14 63.8(2) . . . . ?
C11 C12 C13 C15 -58.5(2) . . . . ?
C12 C7 C8 C9 -5.5(2) . . . . ?
C12 C7 C8 C19 168.86(14) . . . . ?
C13 C5 C6 C1 -176.70(13) . . . . ?
C13 C5 C6 C7 4.73(17) . . . . ?
C16 N1 C1 C2 -4.9(2) . . . . ?
C16 N1 C1 C6 174.83(15) . . . . ?
C16 N1 C17 C18 -100.01(16) . . . . ?
C17 N1 C1 C2 139.89(15) . . . . ?
C17 N1 C1 C6 -40.4(2) . . . . ?
C17 C18 C19 C8 -59.88(17) . . . . ?
C17 C18 C20 O1 58.39(18) . . . . ?
C17 C18 C20 O3 -126.43(14) . . . . ?
C17 C18 C21 O2 -70.33(19) . . . . ?
C17 C18 C21 O4 113.05(15) . . . . ?
C19 C8 C9 C10 -172.14(15) . . . . ?
C19 C18 C20 O1 -59.21(19) . . . . ?
C19 C18 C20 O3 115.97(14) . . . . ?
C19 C18 C21 O2 47.1(2) . . . . ?
C19 C18 C21 O4 -129.49(14) . . . . ?
C20 O3 C22 O4 -46.47(19) . . . . ?
C20 O3 C22 C23 -161.13(14) . . . . ?
C20 O3 C22 C24 74.49(18) . . . . ?
C20 C18 C19 C8 57.79(17) . . . . ?
C20 C18 C21 O2 166.59(15) . . . . ?
C20 C18 C21 O4 -10.03(19) . . . . ?
C21 O4 C22 O3 34.4(2) . . . . ?
C21 O4 C22 C23 149.01(15) . . . . ?
C21 O4 C22 C24 -87.38(17) . . . . ?
C21 C18 C19 C8 179.86(13) . . . . ?
C21 C18 C20 O1 -176.31(14) . . . . ?
C21 C18 C20 O3 -1.13(19) . . . . ?
C22 O3 C20 O1 -153.84(14) . . . . ?
C22 O3 C20 C18 30.8(2) . . . . ?
C22 O4 C21 O2 175.47(14) . . . . ?
C22 O4 C21 C18 -7.7(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 1.033
_oxdiff_exptl_absorpt_empirical_full_min 0.966
####################################################################### 
# 
# 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_jb316abs
_database_code_depnum_ccdc_archive 'CCDC 2069093'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-29
_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        
1,2,3,4-Tetrahydro-1,2,2-trimethyl-spiro[cyclohexan-1,3-acenaphth[5,6-bc]azepine]-2,6-dione
_chemical_formula_moiety         'C21 H21 N O2'
_chemical_formula_sum            'C21 H21 N O2'
_chemical_formula_weight         319.39
_chemical_melting_point          '423 dec.'
_chemical_oxdiff_formula         'C21 H21 N1 O2'
_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      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                   15.2738(6)
_cell_length_b                   10.3218(4)
_cell_length_c                   10.2175(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.356(3)
_cell_angle_gamma                90
_cell_volume                     1608.06(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1666
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.1410
_cell_measurement_theta_min      3.7880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.924
_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    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -9 11 0.2285
-1 -15 1 0.1070
-1 -4 -14 0.2289
1 15 -1 0.1070
1 10 -10 0.1657
1 2 14 0.2248
-21 2 0 0.0691
22 0 -2 0.0641
17 -6 6 0.1397
-10 -8 11 0.2170

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/hexane'
_exptl_crystal_size_max          0.477
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.159
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
-1.9665 -8.9784 10.9861 -0.0482 0.0500 -0.9795
-1.0239 -14.9796 1.0133 0.2792 0.7235 -0.6810
-1.0624 -4.0106 -13.9671 0.2592 0.7724 0.6037
1.0239 14.9796 -1.0133 -0.2792 -0.7235 0.6810
0.9764 9.9769 -9.9895 -0.0312 -0.1193 0.9671
1.0582 2.0133 13.9692 -0.2144 -0.6733 -0.6873
-20.9199 1.9719 -0.0075 -0.9246 0.3175 0.1006
21.9123 0.0245 -1.9902 0.9518 -0.3572 0.0921
16.9506 -5.9648 5.9983 0.7560 -0.2776 -0.5945
-9.9355 -7.9895 10.9830 -0.4058 0.1592 -0.9312

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.820
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6486
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.820
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.369
_diffrn_reflns_theta_min         3.322
_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 0.997
_diffrn_measured_fraction_theta_max 0.820
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     21.00  67.00   1.00   25.00    --   13.74  57.00  30.00   46
  2  ω     -9.00  78.00   1.00   25.00    --   13.74  19.00-180.00   87
  3  ω    -56.00   8.00   1.00   25.00    --   13.74   0.00-180.00   64
;
_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      0.0420758000
_diffrn_orient_matrix_UB_12      -0.0225489000
_diffrn_orient_matrix_UB_13      -0.0152839000
_diffrn_orient_matrix_UB_21      -0.0198390000
_diffrn_orient_matrix_UB_22      -0.0496157000
_diffrn_orient_matrix_UB_23      -0.0395485000
_diffrn_orient_matrix_UB_31      -0.0008517000
_diffrn_orient_matrix_UB_32      0.0417859000
_diffrn_orient_matrix_UB_33      -0.0551590000
_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                2578
_reflns_number_total             3307
_reflns_odcompleteness_completeness 99.64
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.084
_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)+(0.0396P)²+0.4083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1111
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.54288(9) 0.33308(14) 0.47744(12) 0.0399(4) Uani 1 1 d . . . . .
O2 O 0.67226(9) 0.63538(12) 0.72137(13) 0.0357(3) Uani 1 1 d . . . . .
N1 N 0.79195(9) 0.48288(13) 0.53260(14) 0.0247(3) Uani 1 1 d . . . . .
C1 C 0.83768(11) 0.37448(16) 0.48694(16) 0.0220(4) Uani 1 1 d . . . . .
C2 C 0.90545(12) 0.38539(18) 0.40381(17) 0.0287(4) Uani 1 1 d . . . . .
H2 H 0.924929 0.467672 0.382477 0.034 Uiso 1 1 calc R . . . .
C3 C 0.94641(12) 0.27635(18) 0.34982(17) 0.0293(4) Uani 1 1 d . . . . .
H3 H 0.991971 0.287656 0.294378 0.035 Uiso 1 1 calc R . . . .
C4 C 0.91898(11) 0.15502(17) 0.37922(16) 0.0235(4) Uani 1 1 d . . . . .
C5 C 0.85193(10) 0.14278(16) 0.46748(15) 0.0202(4) Uani 1 1 d . . . . .
C6 C 0.82942(11) 0.01217(16) 0.48756(16) 0.0225(4) Uani 1 1 d . . . . .
C7 C 0.76614(12) -0.01550(17) 0.57235(17) 0.0270(4) Uani 1 1 d . . . . .
H7 H 0.749035 -0.100561 0.586651 0.032 Uiso 1 1 calc R . . . .
C8 C 0.72739(11) 0.08827(17) 0.63768(16) 0.0246(4) Uani 1 1 d . . . . .
H8 H 0.686035 0.068738 0.697990 0.029 Uiso 1 1 calc R . . . .
C9 C 0.74698(10) 0.21654(16) 0.61770(15) 0.0200(4) Uani 1 1 d . . . . .
C10 C 0.81095(10) 0.24790(16) 0.52553(15) 0.0195(4) Uani 1 1 d . . . . .
C11 C 0.94413(12) 0.02237(18) 0.33232(18) 0.0275(4) Uani 1 1 d . . . . .
H11A H 1.0065(14) 0.0023(18) 0.3551(18) 0.037(5) Uiso 1 1 d . . . . .
H11B H 0.9367(12) 0.0170(18) 0.2347(19) 0.035(5) Uiso 1 1 d . . . . .
C12 C 0.88351(13) -0.07229(19) 0.4014(2) 0.0290(4) Uani 1 1 d . . . . .
H12A H 0.8453(13) -0.1166(18) 0.3371(19) 0.036(5) Uiso 1 1 d . . . . .
H12B H 0.9163(13) -0.1380(19) 0.4538(18) 0.036(5) Uiso 1 1 d . . . . .
C13 C 0.82543(13) 0.60967(17) 0.4994(2) 0.0361(5) Uani 1 1 d . . . . .
H13A H 0.886752 0.614532 0.525505 0.054 Uiso 1 1 calc GR . . . .
H13B H 0.794271 0.675324 0.544294 0.054 Uiso 1 1 calc GR . . . .
H13C H 0.817399 0.622968 0.406489 0.054 Uiso 1 1 calc GR . . . .
C14 C 0.69617(11) 0.47205(17) 0.51206(16) 0.0239(4) Uani 1 1 d . . . . .
H14A H 0.682688 0.413888 0.439080 0.029 Uiso 1 1 calc R . . . .
H14B H 0.672455 0.556528 0.488113 0.029 Uiso 1 1 calc R . . . .
C15 C 0.71004(11) 0.31866(17) 0.70361(15) 0.0226(4) Uani 1 1 d . . . . .
H15A H 0.758469 0.362711 0.750386 0.027 Uiso 1 1 calc R . . . .
H15B H 0.676030 0.276086 0.768363 0.027 Uiso 1 1 calc R . . . .
C16 C 0.65074(11) 0.42268(16) 0.63131(15) 0.0201(4) Uani 1 1 d . . . . .
C17 C 0.56238(11) 0.36046(16) 0.59062(16) 0.0231(4) Uani 1 1 d . . . . .
C18 C 0.50138(12) 0.33376(18) 0.69745(17) 0.0289(4) Uani 1 1 d . . . . .
H18A H 0.523116 0.260119 0.748601 0.035 Uiso 1 1 calc R . . . .
H18B H 0.444010 0.311239 0.658284 0.035 Uiso 1 1 calc R . . . .
C19 C 0.49246(12) 0.44962(19) 0.78798(17) 0.0326(5) Uani 1 1 d . . . . .
H19A H 0.462386 0.519156 0.739924 0.039 Uiso 1 1 calc R . . . .
H19B H 0.457180 0.425233 0.859950 0.039 Uiso 1 1 calc R . . . .
C20 C 0.58121(13) 0.49768(19) 0.84252(17) 0.0312(4) Uani 1 1 d . . . . .
H20A H 0.573466 0.573912 0.896149 0.037 Uiso 1 1 calc R . . . .
H20B H 0.609335 0.431223 0.897365 0.037 Uiso 1 1 calc R . . . .
C21 C 0.63822(11) 0.53048(18) 0.73198(16) 0.0251(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.211(2) . ?
O2 C21 1.209(2) . ?
N1 C1 1.413(2) . ?
N1 C13 1.452(2) . ?
N1 C14 1.470(2) . ?
C1 C2 1.381(2) . ?
C1 C10 1.431(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.415(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.360(2) . ?
C4 C5 1.409(2) . ?
C4 C11 1.508(2) . ?
C5 C6 1.409(2) . ?
C5 C10 1.402(2) . ?
C6 C7 1.365(2) . ?
C6 C12 1.517(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.410(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.375(2) . ?
C9 C10 1.433(2) . ?
C9 C15 1.503(2) . ?
C11 H11A 0.99(2) . ?
C11 H11B 0.999(19) . ?
C11 C12 1.545(3) . ?
C12 H12A 0.97(2) . ?
C12 H12B 0.98(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C16 1.525(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.562(2) . ?
C16 C17 1.530(2) . ?
C16 C21 1.535(2) . ?
C17 C18 1.502(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.523(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.518(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.505(2) . ?

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 116.68(14) . . ?
C1 N1 C14 113.57(13) . . ?
C13 N1 C14 113.34(14) . . ?
N1 C1 C10 118.53(14) . . ?
C2 C1 N1 122.76(15) . . ?
C2 C1 C10 118.68(16) . . ?
C1 C2 H2 118.7 . . ?
C1 C2 C3 122.62(17) . . ?
C3 C2 H2 118.7 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.83(16) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 117.95(16) . . ?
C3 C4 C11 132.74(16) . . ?
C5 C4 C11 109.28(15) . . ?
C6 C5 C4 111.81(15) . . ?
C10 C5 C4 124.11(16) . . ?
C10 C5 C6 124.06(15) . . ?
C5 C6 C12 108.62(15) . . ?
C7 C6 C5 118.70(15) . . ?
C7 C6 C12 132.66(16) . . ?
C6 C7 H7 120.9 . . ?
C6 C7 C8 118.27(16) . . ?
C8 C7 H7 120.9 . . ?
C7 C8 H8 118.0 . . ?
C9 C8 C7 124.05(16) . . ?
C9 C8 H8 118.0 . . ?
C8 C9 C10 118.53(15) . . ?
C8 C9 C15 119.75(15) . . ?
C10 C9 C15 121.27(15) . . ?
C1 C10 C9 127.14(15) . . ?
C5 C10 C1 116.64(15) . . ?
C5 C10 C9 116.22(15) . . ?
C4 C11 H11A 112.0(11) . . ?
C4 C11 H11B 110.6(11) . . ?
C4 C11 C12 104.98(14) . . ?
H11A C11 H11B 105.9(15) . . ?
C12 C11 H11A 110.8(11) . . ?
C12 C11 H11B 112.7(11) . . ?
C6 C12 C11 105.25(15) . . ?
C6 C12 H12A 109.7(12) . . ?
C6 C12 H12B 111.0(11) . . ?
C11 C12 H12A 110.1(11) . . ?
C11 C12 H12B 112.7(11) . . ?
H12A C12 H12B 108.1(16) . . ?
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 108.7 . . ?
N1 C14 H14B 108.7 . . ?
N1 C14 C16 114.02(13) . . ?
H14A C14 H14B 107.6 . . ?
C16 C14 H14A 108.7 . . ?
C16 C14 H14B 108.7 . . ?
C9 C15 H15A 108.4 . . ?
C9 C15 H15B 108.4 . . ?
C9 C15 C16 115.66(13) . . ?
H15A C15 H15B 107.4 . . ?
C16 C15 H15A 108.4 . . ?
C16 C15 H15B 108.4 . . ?
C14 C16 C15 109.23(13) . . ?
C14 C16 C17 111.01(13) . . ?
C14 C16 C21 111.94(14) . . ?
C17 C16 C15 108.53(13) . . ?
C17 C16 C21 110.11(14) . . ?
C21 C16 C15 105.84(13) . . ?
O1 C17 C16 121.42(16) . . ?
O1 C17 C18 121.54(16) . . ?
C18 C17 C16 117.04(14) . . ?
C17 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C17 C18 C19 112.26(15) . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
C18 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 C18 111.71(15) . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C19 C20 H20A 109.7 . . ?
C19 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C21 C20 C19 109.96(14) . . ?
C21 C20 H20A 109.7 . . ?
C21 C20 H20B 109.7 . . ?
O2 C21 C16 121.21(16) . . ?
O2 C21 C20 122.66(16) . . ?
C20 C21 C16 116.12(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C17 C18 C19 -133.17(18) . . . . ?
N1 C1 C2 C3 -174.76(16) . . . . ?
N1 C1 C10 C5 173.65(14) . . . . ?
N1 C1 C10 C9 -6.7(2) . . . . ?
N1 C14 C16 C15 -36.44(19) . . . . ?
N1 C14 C16 C17 -156.07(14) . . . . ?
N1 C14 C16 C21 80.44(17) . . . . ?
C1 N1 C14 C16 96.40(16) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C1 C10 C5 -4.6(2) . . . . ?
C2 C1 C10 C9 175.10(16) . . . . ?
C2 C3 C4 C5 -2.3(3) . . . . ?
C2 C3 C4 C11 175.45(18) . . . . ?
C3 C4 C5 C6 179.27(15) . . . . ?
C3 C4 C5 C10 0.9(2) . . . . ?
C3 C4 C11 C12 -177.24(19) . . . . ?
C4 C5 C6 C7 179.04(15) . . . . ?
C4 C5 C6 C12 -2.31(19) . . . . ?
C4 C5 C10 C1 2.6(2) . . . . ?
C4 C5 C10 C9 -177.13(14) . . . . ?
C4 C11 C12 C6 -1.92(19) . . . . ?
C5 C4 C11 C12 0.66(19) . . . . ?
C5 C6 C7 C8 -1.1(2) . . . . ?
C5 C6 C12 C11 2.59(19) . . . . ?
C6 C5 C10 C1 -175.59(15) . . . . ?
C6 C5 C10 C9 4.7(2) . . . . ?
C6 C7 C8 C9 2.6(3) . . . . ?
C7 C6 C12 C11 -179.02(19) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C7 C8 C9 C15 -172.78(15) . . . . ?
C8 C9 C10 C1 177.18(16) . . . . ?
C8 C9 C10 C5 -3.1(2) . . . . ?
C8 C9 C15 C16 -120.04(17) . . . . ?
C9 C15 C16 C14 -47.14(19) . . . . ?
C9 C15 C16 C17 74.02(17) . . . . ?
C9 C15 C16 C21 -167.82(14) . . . . ?
C10 C1 C2 C3 3.4(3) . . . . ?
C10 C5 C6 C7 -2.6(2) . . . . ?
C10 C5 C6 C12 176.08(15) . . . . ?
C10 C9 C15 C16 67.7(2) . . . . ?
C11 C4 C5 C6 1.02(19) . . . . ?
C11 C4 C5 C10 -177.37(15) . . . . ?
C12 C6 C7 C8 -179.38(17) . . . . ?
C13 N1 C1 C2 -6.4(2) . . . . ?
C13 N1 C1 C10 175.43(15) . . . . ?
C13 N1 C14 C16 -127.40(16) . . . . ?
C14 N1 C1 C2 128.26(17) . . . . ?
C14 N1 C1 C10 -49.91(19) . . . . ?
C14 C16 C17 O1 13.6(2) . . . . ?
C14 C16 C17 C18 -166.96(14) . . . . ?
C14 C16 C21 O2 -9.3(2) . . . . ?
C14 C16 C21 C20 170.35(14) . . . . ?
C15 C9 C10 C1 -10.5(2) . . . . ?
C15 C9 C10 C5 169.21(14) . . . . ?
C15 C16 C17 O1 -106.44(18) . . . . ?
C15 C16 C17 C18 72.99(18) . . . . ?
C15 C16 C21 O2 109.61(18) . . . . ?
C15 C16 C21 C20 -70.75(18) . . . . ?
C16 C17 C18 C19 47.4(2) . . . . ?
C17 C16 C21 O2 -133.29(17) . . . . ?
C17 C16 C21 C20 46.36(19) . . . . ?
C17 C18 C19 C20 -53.47(19) . . . . ?
C18 C19 C20 C21 56.5(2) . . . . ?
C19 C20 C21 O2 125.10(19) . . . . ?
C19 C20 C21 C16 -54.5(2) . . . . ?
C21 C16 C17 O1 138.14(17) . . . . ?
C21 C16 C17 C18 -42.4(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 1.085
_oxdiff_exptl_absorpt_empirical_full_min 0.943
####################################################################### 
# 
# 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_jb313abs
_database_code_depnum_ccdc_archive 'CCDC 2069090'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 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        
;
6-Dimethylamino-1,2-dihydroacenaphthylene-5-carbaldehyde
;
_chemical_formula_moiety         'C15 H15 N O'
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28
_chemical_melting_point          369-372
_chemical_oxdiff_formula         'C15 H15 N1 O1'
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1836(6)
_cell_length_b                   9.4806(5)
_cell_length_c                   13.2584(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.767(7)
_cell_angle_gamma                90
_cell_volume                     1137.62(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1446
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      28.0360
_cell_measurement_theta_min      3.7780
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
12 1 2 0.0399
-12 -1 -2 0.0399
-1 13 3 0.2178
1 -13 -3 0.2178
-5 10 11 0.2177
-1 -9 14 0.1350
0 10 -12 0.1339
5 -10 -12 0.1892

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.438
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.08
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
12.0000 1.0000 2.0000 -0.8674 0.4022 0.1432
-12.0000 -1.0000 -2.0000 0.8674 -0.4022 -0.1432
-1.0000 13.0000 3.0000 -0.1663 0.0928 -0.9696
1.0000 -13.0000 -3.0000 0.1663 -0.0928 0.9696
-5.0000 10.0000 11.0000 -0.1660 -0.4390 -0.8789
-1.0000 -9.0000 14.0000 -0.3569 -0.7717 0.5414
0.0000 10.0000 -12.0000 0.3404 0.6726 -0.6443
5.0000 -10.0000 -12.0000 0.2023 0.4790 0.8849

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4702
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.249
_diffrn_reflns_theta_min         3.305
_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 0.997
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  78.00   1.00   30.00    --   13.74  37.00  30.00   73
  2  ω      3.00  50.00   1.00   30.00    --   13.74  57.00 -60.00   47
  3  ω     24.00  70.00   1.00   30.00    --   13.74  57.00 120.00   46
  4  ω     37.00  75.00   1.00   30.00    --   13.74  57.00  60.00   38
;
_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      -0.0654518000
_diffrn_orient_matrix_UB_12      -0.0094588000
_diffrn_orient_matrix_UB_13      -0.0362459000
_diffrn_orient_matrix_UB_21      0.0385647000
_diffrn_orient_matrix_UB_22      0.0193216000
_diffrn_orient_matrix_UB_23      -0.0399465000
_diffrn_orient_matrix_UB_31      0.0189282000
_diffrn_orient_matrix_UB_32      -0.0717277000
_diffrn_orient_matrix_UB_33      -0.0060850000
_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                1961
_reflns_number_total             2341
_reflns_odcompleteness_completeness 99.63
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.067
_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)+(0.0471P)²+0.2874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1119
_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)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_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
O1 O 0.10932(12) 0.42141(13) 0.61841(9) 0.0358(3) Uani 1 1 d . . . . .
N1 N 0.23926(14) 0.74130(13) 0.45165(9) 0.0221(3) Uani 1 1 d . . . . .
C1 C 0.39023(16) 0.73110(16) 0.49821(11) 0.0197(3) Uani 1 1 d . . . . .
C2 C 0.49798(18) 0.81290(16) 0.46628(11) 0.0239(4) Uani 1 1 d . . . . .
H2 H 0.469707 0.875147 0.410226 0.029 Uiso 1 1 calc R . . . .
C3 C 0.64806(18) 0.80891(17) 0.51258(12) 0.0250(4) Uani 1 1 d . . . . .
H3 H 0.718927 0.865367 0.486796 0.030 Uiso 1 1 calc R . . . .
C4 C 0.68997(16) 0.72308(16) 0.59470(11) 0.0210(3) Uani 1 1 d . . . . .
C5 C 0.58184(16) 0.63659(15) 0.62709(10) 0.0182(3) Uani 1 1 d . . . . .
C6 C 0.64261(16) 0.55362(16) 0.71227(11) 0.0213(3) Uani 1 1 d . . . . .
C7 C 0.55418(17) 0.46087(17) 0.75266(11) 0.0240(4) Uani 1 1 d . . . . .
H7 H 0.591833 0.406130 0.811323 0.029 Uiso 1 1 calc R . . . .
C8 C 0.40628(17) 0.44881(16) 0.70503(12) 0.0222(4) Uani 1 1 d . . . . .
H8 H 0.345475 0.382233 0.731724 0.027 Uiso 1 1 calc R . . . .
C9 C 0.34389(16) 0.52851(15) 0.62128(11) 0.0188(3) Uani 1 1 d . . . . .
C10 C 0.43224(16) 0.63185(15) 0.58002(10) 0.0176(3) Uani 1 1 d . . . . .
C11 C 0.83706(18) 0.69872(19) 0.66302(13) 0.0259(4) Uani 1 1 d . . . . .
H11A H 0.8754(18) 0.7884(19) 0.6962(13) 0.029(5) Uiso 1 1 d . . . . .
H11B H 0.9127(19) 0.6619(17) 0.6254(13) 0.029(5) Uiso 1 1 d . . . . .
C12 C 0.80532(18) 0.5879(2) 0.74217(13) 0.0293(4) Uani 1 1 d . . . . .
H12A H 0.865(2) 0.504(2) 0.7417(14) 0.043(5) Uiso 1 1 d . . . . .
H12B H 0.826(2) 0.627(2) 0.8135(15) 0.046(5) Uiso 1 1 d . . . . .
C13 C 0.20920(19) 0.80604(19) 0.35068(12) 0.0305(4) Uani 1 1 d . . . . .
H13A H 0.226293 0.907933 0.357079 0.046 Uiso 1 1 calc GR . . . .
H13B H 0.106178 0.788432 0.319628 0.046 Uiso 1 1 calc GR . . . .
H13C H 0.274913 0.765347 0.307364 0.046 Uiso 1 1 calc GR . . . .
C14 C 0.14363(17) 0.80249(18) 0.51796(12) 0.0266(4) Uani 1 1 d . . . . .
H14A H 0.168106 0.761383 0.586561 0.040 Uiso 1 1 calc GR . . . .
H14B H 0.040139 0.782240 0.489572 0.040 Uiso 1 1 calc GR . . . .
H14C H 0.158617 0.904806 0.522126 0.040 Uiso 1 1 calc GR . . . .
C15 C 0.19065(16) 0.49148(16) 0.57478(12) 0.0231(4) Uani 1 1 d . . . . .
H15 H 0.153934 0.524033 0.507501 0.028 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.2167(18) . ?
N1 C1 1.4221(19) . ?
N1 C13 1.4559(19) . ?
N1 C14 1.4637(19) . ?
C1 C2 1.379(2) . ?
C1 C10 1.438(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.411(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.361(2) . ?
C4 C5 1.410(2) . ?
C4 C11 1.511(2) . ?
C5 C6 1.411(2) . ?
C5 C10 1.410(2) . ?
C6 C7 1.366(2) . ?
C6 C12 1.515(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.402(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(2) . ?
C9 C10 1.438(2) . ?
C9 C15 1.480(2) . ?
C11 H11A 0.993(18) . ?
C11 H11B 0.985(17) . ?
C11 C12 1.547(2) . ?
C12 H12A 0.97(2) . ?
C12 H12B 1.004(19) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 0.9500 . ?

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 116.52(12) . . ?
C1 N1 C14 113.98(12) . . ?
C13 N1 C14 110.23(12) . . ?
N1 C1 C10 119.27(13) . . ?
C2 C1 N1 121.74(13) . . ?
C2 C1 C10 118.99(14) . . ?
C1 C2 H2 118.3 . . ?
C1 C2 C3 123.38(14) . . ?
C3 C2 H2 118.3 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.13(14) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 118.23(14) . . ?
C3 C4 C11 132.33(14) . . ?
C5 C4 C11 109.44(13) . . ?
C4 C5 C6 111.38(13) . . ?
C4 C5 C10 124.58(13) . . ?
C10 C5 C6 124.03(13) . . ?
C5 C6 C12 109.18(13) . . ?
C7 C6 C5 119.45(14) . . ?
C7 C6 C12 131.36(14) . . ?
C6 C7 H7 121.0 . . ?
C6 C7 C8 118.08(14) . . ?
C8 C7 H7 121.0 . . ?
C7 C8 H8 118.2 . . ?
C9 C8 C7 123.66(14) . . ?
C9 C8 H8 118.2 . . ?
C8 C9 C10 119.57(14) . . ?
C8 C9 C15 116.08(13) . . ?
C10 C9 C15 124.14(13) . . ?
C5 C10 C1 115.43(13) . . ?
C5 C10 C9 115.07(13) . . ?
C9 C10 C1 129.50(14) . . ?
C4 C11 H11A 110.4(10) . . ?
C4 C11 H11B 112.7(10) . . ?
C4 C11 C12 104.96(13) . . ?
H11A C11 H11B 107.4(14) . . ?
C12 C11 H11A 112.0(10) . . ?
C12 C11 H11B 109.5(10) . . ?
C6 C12 C11 105.01(13) . . ?
C6 C12 H12A 111.2(11) . . ?
C6 C12 H12B 110.5(11) . . ?
C11 C12 H12A 112.3(11) . . ?
C11 C12 H12B 111.0(11) . . ?
H12A C12 H12B 107.0(16) . . ?
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 . . ?
O1 C15 C9 123.27(14) . . ?
O1 C15 H15 118.4 . . ?
C9 C15 H15 118.4 . . ?

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 177.98(14) . . . . ?
N1 C1 C10 C5 -175.17(12) . . . . ?
N1 C1 C10 C9 4.6(2) . . . . ?
C1 C2 C3 C4 -1.7(2) . . . . ?
C2 C1 C10 C5 5.5(2) . . . . ?
C2 C1 C10 C9 -174.73(14) . . . . ?
C2 C3 C4 C5 2.9(2) . . . . ?
C2 C3 C4 C11 -177.24(15) . . . . ?
C3 C4 C5 C6 179.63(13) . . . . ?
C3 C4 C5 C10 0.3(2) . . . . ?
C3 C4 C11 C12 179.45(17) . . . . ?
C4 C5 C6 C7 -178.57(13) . . . . ?
C4 C5 C6 C12 1.15(17) . . . . ?
C4 C5 C10 C1 -4.5(2) . . . . ?
C4 C5 C10 C9 175.69(13) . . . . ?
C4 C11 C12 C6 1.27(17) . . . . ?
C5 C4 C11 C12 -0.66(17) . . . . ?
C5 C6 C7 C8 2.1(2) . . . . ?
C5 C6 C12 C11 -1.49(18) . . . . ?
C6 C5 C10 C1 176.26(13) . . . . ?
C6 C5 C10 C9 -3.5(2) . . . . ?
C6 C7 C8 C9 -1.9(2) . . . . ?
C7 C6 C12 C11 178.17(16) . . . . ?
C7 C8 C9 C10 -1.0(2) . . . . ?
C7 C8 C9 C15 174.06(14) . . . . ?
C8 C9 C10 C1 -176.20(14) . . . . ?
C8 C9 C10 C5 3.6(2) . . . . ?
C8 C9 C15 O1 17.4(2) . . . . ?
C10 C1 C2 C3 -2.7(2) . . . . ?
C10 C5 C6 C7 0.7(2) . . . . ?
C10 C5 C6 C12 -179.54(14) . . . . ?
C10 C9 C15 O1 -167.81(14) . . . . ?
C11 C4 C5 C6 -0.28(17) . . . . ?
C11 C4 C5 C10 -179.59(13) . . . . ?
C12 C6 C7 C8 -177.58(16) . . . . ?
C13 N1 C1 C2 18.8(2) . . . . ?
C13 N1 C1 C10 -160.48(13) . . . . ?
C14 N1 C1 C2 -111.32(16) . . . . ?
C14 N1 C1 C10 69.37(17) . . . . ?
C15 C9 C10 C1 9.2(2) . . . . ?
C15 C9 C10 C5 -171.08(13) . . . . ?

_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 1.055
_oxdiff_exptl_absorpt_empirical_full_min 0.939
####################################################################### 
# 
# 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_jb300regrowabs
_database_code_depnum_ccdc_archive 'CCDC 2069099'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 downloaded from the CCDC.
;
_audit_creation_date             2019-09-17
_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_systematic        
;
3-Nitro-1,2,3,4-tetrahydro-1,8,8-trimethyl-8H-fluoreno[4,5-bcd]azocine
;
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H20 N2 O2'
_chemical_formula_sum            'C19 H20 N2 O2'
_chemical_formula_weight         308.37
_chemical_absolute_configuration unk
_chemical_melting_point          388-391
_chemical_oxdiff_formula         'C20 H20 N2 O2'
_chemical_oxdiff_usercomment     'Colourless 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.7431(3)
_cell_length_b                   6.9459(2)
_cell_length_c                   12.1403(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.257(4)
_cell_angle_gamma                90
_cell_volume                     792.63(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3758
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      29.5400
_cell_measurement_theta_min      3.8010
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.927
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
13 1 0 0.0328
-13 -1 0 0.0328
4 3 -16 0.1073
-2 10 4 0.1515
1 -10 0 0.1166
-3 0 17 0.0487
3 -1 -17 0.0682

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.066
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
13.0000 1.0000 -0.0000 -0.6503 -0.7410 0.0121
-13.0000 -1.0000 0.0000 0.6503 0.7410 -0.0121
4.0000 3.0000 -16.0000 -0.0632 -0.0634 -0.9809
-2.0000 10.0000 4.0000 0.7731 -0.7060 -0.0959
1.0000 -10.0000 0.0000 -0.7083 0.6679 0.3175
-3.0000 0.0000 17.0000 0.2066 -0.2263 0.9462
3.0000 -1.0000 -17.0000 -0.2719 0.2983 -0.9148

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8479
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.350
_diffrn_reflns_theta_min         3.410
_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 0.997
_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    -37.00  47.00   1.00   60.00    --  -19.97  57.00 -90.00   84
  2  ω    -37.00  47.00   1.00   60.00    --  -19.97  57.00-180.00   84
  3  ω      3.00  87.00   1.00   60.00    --   20.05  57.00   0.00   84
  4  φ     45.00 120.00   1.00   60.00  20.05  20.05  40.00    --    75
  5  ω    -87.00  -3.00   1.00   60.00    --  -19.97 -57.00 120.00   84
  6  ω      3.00  37.00   1.00   60.00    --   20.05  57.00 -90.00   34
  7  ω    -51.00  49.00   1.00   60.00    --   20.05 -19.00   0.00  100
;
_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      -0.0550485000
_diffrn_orient_matrix_UB_12      0.0653208000
_diffrn_orient_matrix_UB_13      0.0024380000
_diffrn_orient_matrix_UB_21      -0.0514632000
_diffrn_orient_matrix_UB_22      -0.0719377000
_diffrn_orient_matrix_UB_23      -0.0223946000
_diffrn_orient_matrix_UB_31      0.0033476000
_diffrn_orient_matrix_UB_32      -0.0314201000
_diffrn_orient_matrix_UB_33      0.0562506000
_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         0.809
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                2904
_reflns_number_total             3165
_reflns_odcompleteness_completeness 99.76
_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         0.202
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1088 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3165
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.077
_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)+(0.0369P)²+0.1990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0961
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11), C3(H3), C4(H4), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_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
O2 O 0.8974(3) 0.0490(4) 0.8079(2) 0.0523(7) Uani 1 1 d . . . . .
N1 N 0.7365(2) 0.5372(4) 0.85795(19) 0.0234(5) Uani 1 1 d . . . . .
N2 N 0.8539(3) 0.1896(4) 0.7494(2) 0.0330(6) Uani 1 1 d . . . . .
O1 O 0.9263(2) 0.2874(4) 0.7031(2) 0.0495(7) Uani 1 1 d . . . . .
C6 C 0.4974(3) 0.6720(4) 0.7806(2) 0.0192(6) Uani 1 1 d . . . . .
C7 C 0.4345(3) 0.5518(4) 0.6776(2) 0.0205(6) Uani 1 1 d . . . . .
C12 C 0.2898(3) 0.6025(4) 0.6390(2) 0.0231(6) Uani 1 1 d . . . . .
C5 C 0.3920(3) 0.7987(4) 0.7955(2) 0.0218(6) Uani 1 1 d . . . . .
C1 C 0.6332(3) 0.6768(4) 0.8602(2) 0.0212(6) Uani 1 1 d . . . . .
C8 C 0.4908(3) 0.4221(4) 0.6127(2) 0.0230(6) Uani 1 1 d . . . . .
C13 C 0.2505(3) 0.7601(4) 0.7103(2) 0.0259(6) Uani 1 1 d . . . . .
C2 C 0.6585(3) 0.8227(4) 0.9421(2) 0.0247(6) Uani 1 1 d . . . . .
H2 H 0.748673 0.833636 0.992088 0.030 Uiso 1 1 calc R . . . .
C11 C 0.2012(3) 0.5192(4) 0.5436(3) 0.0296(7) Uani 1 1 d . . . . .
H11 H 0.105610 0.553129 0.520331 0.036 Uiso 1 1 calc R . . . .
C18 C 0.6995(3) 0.2442(4) 0.7360(2) 0.0269(7) Uani 1 1 d . . . . .
H18 H 0.641618 0.126857 0.723084 0.032 Uiso 1 1 calc R . . . .
C3 C 0.5537(3) 0.9520(4) 0.9512(2) 0.0277(7) Uani 1 1 d . . . . .
H3 H 0.574620 1.048545 1.006215 0.033 Uiso 1 1 calc R . . . .
C17 C 0.6877(3) 0.3376(4) 0.8468(2) 0.0255(7) Uani 1 1 d . . . . .
H17A H 0.589324 0.333301 0.849982 0.031 Uiso 1 1 calc R . . . .
H17B H 0.743751 0.263918 0.910879 0.031 Uiso 1 1 calc R . . . .
C19 C 0.6481(3) 0.3758(4) 0.6349(2) 0.0269(7) Uani 1 1 d . . . . .
H19A H 0.664936 0.315187 0.567700 0.032 Uiso 1 1 calc R . . . .
H19B H 0.702272 0.494593 0.648506 0.032 Uiso 1 1 calc R . . . .
C4 C 0.4189(3) 0.9383(4) 0.8795(2) 0.0267(7) Uani 1 1 d . . . . .
H4 H 0.347192 1.021311 0.887458 0.032 Uiso 1 1 calc R . . . .
C9 C 0.3983(3) 0.3407(4) 0.5166(3) 0.0301(7) Uani 1 1 d . . . . .
H9 H 0.434431 0.253036 0.473508 0.036 Uiso 1 1 calc R . . . .
C10 C 0.2558(3) 0.3849(5) 0.4828(3) 0.0327(7) Uani 1 1 d . . . . .
H10 H 0.196584 0.324665 0.419500 0.039 Uiso 1 1 calc R . . . .
C16 C 0.8789(3) 0.5651(5) 0.9317(3) 0.0340(7) Uani 1 1 d . . . . .
H16A H 0.912783 0.690551 0.918687 0.051 Uiso 1 1 calc GR . . . .
H16B H 0.941324 0.468806 0.915194 0.051 Uiso 1 1 calc GR . . . .
H16C H 0.876648 0.554186 1.010074 0.051 Uiso 1 1 calc GR . . . .
C15 C 0.1410(3) 0.6904(5) 0.7717(3) 0.0375(8) Uani 1 1 d . . . . .
H15A H 0.053457 0.659880 0.716319 0.056 Uiso 1 1 calc GR . . . .
H15B H 0.124292 0.789919 0.821452 0.056 Uiso 1 1 calc GR . . . .
H15C H 0.176502 0.577590 0.815665 0.056 Uiso 1 1 calc GR . . . .
C14 C 0.1957(4) 0.9393(5) 0.6385(3) 0.0398(8) Uani 1 1 d . . . . .
H14A H 0.267703 0.985521 0.604181 0.060 Uiso 1 1 calc GR . . . .
H14B H 0.173406 1.037741 0.686498 0.060 Uiso 1 1 calc GR . . . .
H14C H 0.111753 0.906903 0.579711 0.060 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
O2 N2 1.217(4) . ?
N1 C1 1.403(4) . ?
N1 C17 1.460(4) . ?
N1 C16 1.453(4) . ?
N2 O1 1.218(4) . ?
N2 C18 1.518(4) . ?
C6 C7 1.494(4) . ?
C6 C5 1.400(4) . ?
C6 C1 1.419(4) . ?
C7 C12 1.408(4) . ?
C7 C8 1.401(4) . ?
C12 C13 1.506(4) . ?
C12 C11 1.377(4) . ?
C5 C13 1.514(4) . ?
C5 C4 1.382(4) . ?
C1 C2 1.396(4) . ?
C8 C19 1.519(4) . ?
C8 C9 1.393(4) . ?
C13 C15 1.532(4) . ?
C13 C14 1.533(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.380(4) . ?
C18 H18 0.9800 . ?
C18 C17 1.525(4) . ?
C18 C19 1.506(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C4 H4 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.376(4) . ?
C10 H10 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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 C17 116.1(2) . . ?
C1 N1 C16 118.0(2) . . ?
C16 N1 C17 114.7(2) . . ?
O2 N2 O1 124.2(3) . . ?
O2 N2 C18 116.5(3) . . ?
O1 N2 C18 119.3(3) . . ?
C5 C6 C7 107.8(2) . . ?
C5 C6 C1 118.8(2) . . ?
C1 C6 C7 133.4(2) . . ?
C12 C7 C6 107.1(2) . . ?
C8 C7 C6 134.0(2) . . ?
C8 C7 C12 118.7(3) . . ?
C7 C12 C13 112.0(3) . . ?
C11 C12 C7 121.7(3) . . ?
C11 C12 C13 126.2(3) . . ?
C6 C5 C13 111.6(2) . . ?
C4 C5 C6 122.3(3) . . ?
C4 C5 C13 126.2(3) . . ?
N1 C1 C6 121.0(2) . . ?
C2 C1 N1 121.5(2) . . ?
C2 C1 C6 117.5(2) . . ?
C7 C8 C19 124.2(3) . . ?
C9 C8 C7 118.0(3) . . ?
C9 C8 C19 117.6(2) . . ?
C12 C13 C5 101.4(2) . . ?
C12 C13 C15 111.4(3) . . ?
C12 C13 C14 111.5(2) . . ?
C5 C13 C15 110.4(2) . . ?
C5 C13 C14 111.3(3) . . ?
C15 C13 C14 110.5(3) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 C1 122.1(3) . . ?
C3 C2 H2 118.9 . . ?
C12 C11 H11 120.3 . . ?
C12 C11 C10 119.3(3) . . ?
C10 C11 H11 120.3 . . ?
N2 C18 H18 108.7 . . ?
N2 C18 C17 108.3(2) . . ?
C17 C18 H18 108.7 . . ?
C19 C18 N2 110.3(2) . . ?
C19 C18 H18 108.7 . . ?
C19 C18 C17 112.0(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
N1 C17 C18 112.8(2) . . ?
N1 C17 H17A 109.0 . . ?
N1 C17 H17B 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C8 C19 H19A 109.2 . . ?
C8 C19 H19B 109.2 . . ?
C18 C19 C8 112.1(2) . . ?
C18 C19 H19A 109.2 . . ?
C18 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C5 C4 H4 120.6 . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4 120.6 . . ?
C8 C9 H9 118.7 . . ?
C10 C9 C8 122.6(3) . . ?
C10 C9 H9 118.7 . . ?
C11 C10 H10 120.3 . . ?
C9 C10 C11 119.5(3) . . ?
C9 C10 H10 120.3 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O2 N2 C18 C17 75.0(3) . . . . ?
O2 N2 C18 C19 -162.0(3) . . . . ?
N1 C1 C2 C3 -174.6(3) . . . . ?
N2 C18 C17 N1 77.9(3) . . . . ?
N2 C18 C19 C8 175.6(2) . . . . ?
O1 N2 C18 C17 -104.2(3) . . . . ?
O1 N2 C18 C19 18.7(4) . . . . ?
C6 C7 C12 C13 1.8(3) . . . . ?
C6 C7 C12 C11 179.0(3) . . . . ?
C6 C7 C8 C19 -2.0(5) . . . . ?
C6 C7 C8 C9 -177.1(3) . . . . ?
C6 C5 C13 C12 -3.4(3) . . . . ?
C6 C5 C13 C15 114.7(3) . . . . ?
C6 C5 C13 C14 -122.2(3) . . . . ?
C6 C5 C4 C3 -0.4(4) . . . . ?
C6 C1 C2 C3 4.0(4) . . . . ?
C7 C6 C5 C13 4.7(3) . . . . ?
C7 C6 C5 C4 -175.8(2) . . . . ?
C7 C6 C1 N1 -6.8(4) . . . . ?
C7 C6 C1 C2 174.6(3) . . . . ?
C7 C12 C13 C5 0.8(3) . . . . ?
C7 C12 C13 C15 -116.6(3) . . . . ?
C7 C12 C13 C14 119.4(3) . . . . ?
C7 C12 C11 C10 -1.1(4) . . . . ?
C7 C8 C19 C18 76.0(4) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
C12 C7 C8 C19 171.3(3) . . . . ?
C12 C7 C8 C9 -3.9(4) . . . . ?
C12 C11 C10 C9 -1.9(5) . . . . ?
C5 C6 C7 C12 -4.0(3) . . . . ?
C5 C6 C7 C8 169.8(3) . . . . ?
C5 C6 C1 N1 171.8(2) . . . . ?
C5 C6 C1 C2 -6.8(4) . . . . ?
C1 N1 C17 C18 115.9(3) . . . . ?
C1 C6 C7 C12 174.7(3) . . . . ?
C1 C6 C7 C8 -11.5(5) . . . . ?
C1 C6 C5 C13 -174.2(2) . . . . ?
C1 C6 C5 C4 5.2(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C8 C7 C12 C13 -173.1(2) . . . . ?
C8 C7 C12 C11 4.1(4) . . . . ?
C8 C9 C10 C11 2.0(5) . . . . ?
C13 C12 C11 C10 175.6(3) . . . . ?
C13 C5 C4 C3 179.0(3) . . . . ?
C2 C3 C4 C5 -2.7(4) . . . . ?
C11 C12 C13 C5 -176.2(3) . . . . ?
C11 C12 C13 C15 66.4(4) . . . . ?
C11 C12 C13 C14 -57.6(4) . . . . ?
C17 N1 C1 C6 -46.0(3) . . . . ?
C17 N1 C1 C2 132.6(3) . . . . ?
C17 C18 C19 C8 -63.7(3) . . . . ?
C19 C8 C9 C10 -174.5(3) . . . . ?
C19 C18 C17 N1 -43.9(3) . . . . ?
C4 C5 C13 C12 177.1(3) . . . . ?
C4 C5 C13 C15 -64.8(4) . . . . ?
C4 C5 C13 C14 58.4(4) . . . . ?
C9 C8 C19 C18 -108.8(3) . . . . ?
C16 N1 C1 C6 172.0(2) . . . . ?
C16 N1 C1 C2 -9.4(4) . . . . ?
C16 N1 C17 C18 -100.9(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 1.108
_oxdiff_exptl_absorpt_empirical_full_min 0.896

####################################################################### 
# 
# 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_jb286abs
_database_code_depnum_ccdc_archive 'CCDC 2069096'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 downloaded from the CCDC.
;
_audit_creation_date             2019-09-16
_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        
;
4-(dimethylamino)-9,9-dimethyl-9H-fluorene-5-carbaldehyde
;
_chemical_formula_moiety         'C18 H19 N O'
_chemical_formula_sum            'C18 H19 N O'
_chemical_formula_weight         265.34
_chemical_absolute_configuration unk
_chemical_melting_point          353-356
_chemical_oxdiff_formula         'C18 N1 O1 H19'
_chemical_oxdiff_usercomment     'Yellow Needle'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           110
_space_group_name_H-M_alt        'I 41 c d'
_space_group_name_Hall           'I 4bw -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-y, x+1/2, z+1/4'
'y+1/2, -x, z+3/4'
'x, -y, z+1/2'
'-x+1/2, y+1/2, z'
'-y, -x+1/2, z+3/4'
'y+1/2, x, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1, z+1'
'-y+1/2, x+1, z+3/4'
'y+1, -x+1/2, z+5/4'
'x+1/2, -y+1/2, z+1'
'-x+1, y+1, z+1/2'
'-y+1/2, -x+1, z+5/4'
'y+1, x+1/2, z+3/4'

_cell_length_a                   24.79560(10)
_cell_length_b                   24.79560(10)
_cell_length_c                   9.47440(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5825.07(8)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    7029
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      71.9580
_cell_measurement_theta_min      5.0360
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.852
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.897
_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            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2272
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-14 6 2 0.0676
14 -6 -2 0.0676
-1 -3 -6 0.1202
1 3 6 0.1202
5 15 -1 0.0643
-5 -15 0 0.0167
3 2 -6 0.1111
-15 5 0 0.0462

_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.099
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
-14.0001 6.0000 2.0000 -0.0222 -0.9008 -0.4350
14.0001 -6.0000 -2.0000 0.0222 0.9008 0.4350
-0.9999 -3.0000 -6.0000 -0.0242 -0.1088 0.9881
0.9999 3.0000 6.0000 0.0242 0.1088 -0.9881
4.9999 15.0001 -1.0000 0.9952 -0.0442 -0.0157
-4.9999 -15.0001 0.0000 -0.9670 0.0252 0.1746
3.0001 2.0000 -6.0000 0.3495 0.0182 0.9368
-15.0000 4.9999 -0.0000 -0.0450 -0.9758 -0.1076

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13777
_diffrn_reflns_point_group_measured_fraction_full 0.837
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        66.548
_diffrn_reflns_theta_max         66.548
_diffrn_reflns_theta_min         3.565
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -101.00 -17.00   1.00   25.00    --  -33.50 -57.00  90.00   84
  2  ω     20.00 104.00   1.00   25.00    --   36.58  57.00-180.00   84
  3  ω    -30.00  57.00   1.00   25.00    --   36.58 -65.00 -62.50   87
  4  ω     91.00 176.00   1.00  100.00    --  108.00  45.00-180.00   85
  5  ω     42.00 128.00   1.00  100.00    --  108.00 -65.00  96.86   86
  6  ω     91.00 176.00   1.00  100.00    --  108.00  45.00-150.00   85
  7  ω     41.00 126.00   1.00  100.00    --  108.00 -61.00-180.00   85
  8  ω     87.00 178.00   1.00  100.00    --  108.00  30.00 120.00   91
  9  ω     40.00 125.00   1.00  100.00    --  108.00 -45.00  30.00   85
 10  ω     91.00 176.00   1.00  100.00    --  108.00  45.00 -90.00   85
 11  ω     42.00 128.00   1.00  100.00    --  108.00 -65.00 -90.13   86
 12  ω    -30.00   1.00   1.00   25.00    --   36.58 -61.00 164.14   31
 13  ω     18.00 103.00   1.00   25.00    --   36.58  63.00 -62.16   85
;
_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      0.0220384000
_diffrn_orient_matrix_UB_12      0.0571186000
_diffrn_orient_matrix_UB_13      -0.0281965000
_diffrn_orient_matrix_UB_21      0.0580414000
_diffrn_orient_matrix_UB_22      -0.0210297000
_diffrn_orient_matrix_UB_23      0.0189763000
_diffrn_orient_matrix_UB_31      0.0029645000
_diffrn_orient_matrix_UB_32      -0.0126256000
_diffrn_orient_matrix_UB_33      -0.1588578000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.581
_reflns_Friedel_fraction_full    0.661
_reflns_Friedel_fraction_max     0.661
_reflns_number_gt                2108
_reflns_number_total             2152
_reflns_odcompleteness_completeness 96.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.65
_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         0.128
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 739 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.27(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2152
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.072
_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)+(0.0488P)²+1.3486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0803
_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:
 C18(H18), C2(H2), C4(H4), C11(H11), C3(H3), C10(H10), C9(H9)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C14(H14A,H14B,
 H14C)
;
_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
O1 O 0.41331(8) 0.55733(7) 0.3983(2) 0.0508(5) Uani 1 1 d . . . . .
N1 N 0.41652(6) 0.42334(7) 0.3790(2) 0.0295(4) Uani 1 1 d . . . . .
C6 C 0.32512(7) 0.40864(8) 0.4635(2) 0.0240(4) Uani 1 1 d . . . . .
C7 C 0.31232(7) 0.46274(8) 0.5184(2) 0.0254(4) Uani 1 1 d . . . . .
C1 C 0.37036(7) 0.38956(8) 0.3906(2) 0.0248(4) Uani 1 1 d . . . . .
C8 C 0.33656(8) 0.51316(8) 0.4966(3) 0.0291(5) Uani 1 1 d . . . . .
C5 C 0.28264(7) 0.37407(8) 0.4974(2) 0.0268(5) Uani 1 1 d . . . . .
C13 C 0.24146(8) 0.40223(9) 0.5903(3) 0.0343(5) Uani 1 1 d . . . . .
C18 C 0.37717(9) 0.52444(8) 0.3848(3) 0.0329(5) Uani 1 1 d . . . . .
H18 H 0.374846 0.505436 0.300384 0.039 Uiso 1 1 calc R . . . .
C2 C 0.36804(8) 0.33739(8) 0.3367(3) 0.0310(5) Uani 1 1 d . . . . .
H2 H 0.396674 0.324347 0.283261 0.037 Uiso 1 1 calc R . . . .
C4 C 0.28110(8) 0.32186(8) 0.4457(3) 0.0330(5) Uani 1 1 d . . . . .
H4 H 0.252416 0.299076 0.466728 0.040 Uiso 1 1 calc R . . . .
C12 C 0.26564(8) 0.45842(9) 0.6003(3) 0.0316(5) Uani 1 1 d . . . . .
C11 C 0.24578(9) 0.50304(11) 0.6727(3) 0.0404(5) Uani 1 1 d . . . . .
H11 H 0.215093 0.500059 0.728622 0.048 Uiso 1 1 calc R . . . .
C17 C 0.44586(9) 0.42864(9) 0.5119(3) 0.0339(5) Uani 1 1 d . . . . .
H17A H 0.420868 0.436048 0.586831 0.051 Uiso 1 1 calc GR . . . .
H17B H 0.471298 0.457692 0.504668 0.051 Uiso 1 1 calc GR . . . .
H17C H 0.464693 0.395661 0.531588 0.051 Uiso 1 1 calc GR . . . .
C3 C 0.32357(9) 0.30439(8) 0.3614(3) 0.0365(5) Uani 1 1 d . . . . .
H3 H 0.322252 0.270236 0.320936 0.044 Uiso 1 1 calc R . . . .
C10 C 0.27228(10) 0.55180(10) 0.6604(3) 0.0419(6) Uani 1 1 d . . . . .
H10 H 0.260407 0.581349 0.712272 0.050 Uiso 1 1 calc R . . . .
C15 C 0.18576(8) 0.40464(11) 0.5172(4) 0.0463(7) Uani 1 1 d . . . . .
H15A H 0.189011 0.423492 0.429098 0.069 Uiso 1 1 calc GR . . . .
H15B H 0.160644 0.423252 0.576972 0.069 Uiso 1 1 calc GR . . . .
H15C H 0.173033 0.368659 0.500070 0.069 Uiso 1 1 calc GR . . . .
C9 C 0.31621(9) 0.55717(9) 0.5720(3) 0.0369(6) Uani 1 1 d . . . . .
H9 H 0.332586 0.590714 0.562352 0.044 Uiso 1 1 calc R . . . .
C16 C 0.45285(9) 0.41264(12) 0.2620(3) 0.0447(6) Uani 1 1 d . . . . .
H16A H 0.471601 0.379356 0.278452 0.067 Uiso 1 1 calc GR . . . .
H16B H 0.478462 0.441514 0.254095 0.067 Uiso 1 1 calc GR . . . .
H16C H 0.432480 0.409973 0.176105 0.067 Uiso 1 1 calc GR . . . .
C14 C 0.23660(12) 0.37460(13) 0.7347(3) 0.0560(8) Uani 1 1 d . . . . .
H14A H 0.224151 0.338259 0.722058 0.084 Uiso 1 1 calc GR . . . .
H14B H 0.211387 0.394065 0.792285 0.084 Uiso 1 1 calc GR . . . .
H14C H 0.271223 0.374190 0.780017 0.084 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 C18 1.218(3) . ?
N1 C1 1.423(2) . ?
N1 C17 1.460(3) . ?
N1 C16 1.453(3) . ?
C6 C7 1.474(3) . ?
C6 C1 1.400(3) . ?
C6 C5 1.396(3) . ?
C7 C8 1.403(3) . ?
C7 C12 1.397(3) . ?
C1 C2 1.392(3) . ?
C8 C18 1.488(3) . ?
C8 C9 1.399(3) . ?
C5 C13 1.518(3) . ?
C5 C4 1.385(3) . ?
C13 C12 1.520(3) . ?
C13 C15 1.546(3) . ?
C13 C14 1.534(4) . ?
C18 H18 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.393(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.391(3) . ?
C12 C11 1.392(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.381(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.381(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C9 H9 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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 C17 112.80(17) . . ?
C1 N1 C16 116.73(19) . . ?
C16 N1 C17 111.45(17) . . ?
C1 C6 C7 130.90(18) . . ?
C5 C6 C7 108.37(18) . . ?
C5 C6 C1 120.73(18) . . ?
C8 C7 C6 131.8(2) . . ?
C12 C7 C6 107.75(18) . . ?
C12 C7 C8 120.35(19) . . ?
C6 C1 N1 118.93(18) . . ?
C2 C1 N1 123.52(18) . . ?
C2 C1 C6 117.52(17) . . ?
C7 C8 C18 124.25(19) . . ?
C9 C8 C7 117.7(2) . . ?
C9 C8 C18 117.46(19) . . ?
C6 C5 C13 111.02(18) . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 C13 128.08(19) . . ?
C5 C13 C12 101.08(16) . . ?
C5 C13 C15 111.0(2) . . ?
C5 C13 C14 111.36(19) . . ?
C12 C13 C15 110.17(18) . . ?
C12 C13 C14 112.7(2) . . ?
C14 C13 C15 110.3(2) . . ?
O1 C18 C8 123.3(2) . . ?
O1 C18 H18 118.4 . . ?
C8 C18 H18 118.4 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.1(2) . . ?
C3 C2 H2 119.4 . . ?
C5 C4 H4 120.9 . . ?
C5 C4 C3 118.28(19) . . ?
C3 C4 H4 120.9 . . ?
C7 C12 C13 111.27(18) . . ?
C11 C12 C7 120.4(2) . . ?
C11 C12 C13 128.3(2) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 C12 119.1(2) . . ?
C10 C11 H11 120.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.85(19) . . ?
C4 C3 H3 119.6 . . ?
C11 C10 H10 119.6 . . ?
C9 C10 C11 120.7(2) . . ?
C9 C10 H10 119.6 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.3(2) . . ?
C10 C9 H9 119.4 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 174.4(2) . . . . ?
C6 C7 C8 C18 12.4(4) . . . . ?
C6 C7 C8 C9 -176.4(2) . . . . ?
C6 C7 C12 C13 -6.4(2) . . . . ?
C6 C7 C12 C11 176.2(2) . . . . ?
C6 C1 C2 C3 -3.6(3) . . . . ?
C6 C5 C13 C12 1.9(2) . . . . ?
C6 C5 C13 C15 118.7(2) . . . . ?
C6 C5 C13 C14 -118.0(2) . . . . ?
C6 C5 C4 C3 1.3(3) . . . . ?
C7 C6 C1 N1 9.6(3) . . . . ?
C7 C6 C1 C2 -172.3(2) . . . . ?
C7 C6 C5 C13 -5.7(2) . . . . ?
C7 C6 C5 C4 173.0(2) . . . . ?
C7 C8 C18 O1 -148.2(2) . . . . ?
C7 C8 C9 C10 -2.7(3) . . . . ?
C7 C12 C11 C10 1.2(3) . . . . ?
C1 C6 C7 C8 11.6(4) . . . . ?
C1 C6 C7 C12 -171.6(2) . . . . ?
C1 C6 C5 C13 173.50(19) . . . . ?
C1 C6 C5 C4 -7.8(3) . . . . ?
C1 C2 C3 C4 -2.7(4) . . . . ?
C8 C7 C12 C13 170.8(2) . . . . ?
C8 C7 C12 C11 -6.6(3) . . . . ?
C5 C6 C7 C8 -169.3(2) . . . . ?
C5 C6 C7 C12 7.5(2) . . . . ?
C5 C6 C1 N1 -169.39(19) . . . . ?
C5 C6 C1 C2 8.7(3) . . . . ?
C5 C13 C12 C7 2.9(2) . . . . ?
C5 C13 C12 C11 -180.0(2) . . . . ?
C5 C4 C3 C2 3.8(3) . . . . ?
C13 C5 C4 C3 179.8(2) . . . . ?
C13 C12 C11 C10 -175.7(2) . . . . ?
C18 C8 C9 C10 169.1(2) . . . . ?
C4 C5 C13 C12 -176.8(2) . . . . ?
C4 C5 C13 C15 -59.9(3) . . . . ?
C4 C5 C13 C14 63.4(3) . . . . ?
C12 C7 C8 C18 -164.0(2) . . . . ?
C12 C7 C8 C9 7.2(3) . . . . ?
C12 C11 C10 C9 3.3(4) . . . . ?
C11 C10 C9 C8 -2.6(4) . . . . ?
C17 N1 C1 C6 72.4(2) . . . . ?
C17 N1 C1 C2 -105.6(2) . . . . ?
C15 C13 C12 C7 -114.5(2) . . . . ?
C15 C13 C12 C11 62.6(3) . . . . ?
C9 C8 C18 O1 40.6(3) . . . . ?
C16 N1 C1 C6 -156.6(2) . . . . ?
C16 N1 C1 C2 25.4(3) . . . . ?
C14 C13 C12 C7 121.9(2) . . . . ?
C14 C13 C12 C11 -61.0(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 1.204
_oxdiff_exptl_absorpt_empirical_full_min 0.901
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/hexane'
####################################################################### 
# 
# 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_jb288absbeam
_database_code_depnum_ccdc_archive 'CCDC 2069097'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 downloaded from the CCDC.
;
_audit_creation_date             2019-09-16
_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-2-((4-(dimethylamino)-9,9-dimethyl-9H-fluoren-5-yl) propenenitrile
;
_chemical_formula_moiety         'C21 H19 N3'
_chemical_formula_sum            'C21 H19 N3'
_chemical_formula_weight         313.39
_chemical_melting_point          395-398
_chemical_oxdiff_formula         'C21 H19 N3'
_chemical_oxdiff_usercomment     'Orange Block cut'
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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   18.4256(4)
_cell_length_b                   11.2921(3)
_cell_length_c                   16.4939(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.223(2)
_cell_angle_gamma                90
_cell_volume                     3387.42(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3863
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.3010
_cell_measurement_theta_min      2.9850
_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  0.913
_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    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 6 22 0.1434
-7 8 19 0.1034
-2 15 -6 0.1511
0 -15 6 0.1475
26 -1 -6 0.1174
20 -7 9 0.1342
-26 0 6 0.1521
-20 8 -6 0.1881
0 -6 -22 0.1434

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/hexane'
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.277
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
0.0093 6.0021 21.9891 -0.9899 0.2495 -0.1342
-6.9935 8.0008 18.9891 -0.8418 0.1918 -0.4401
-2.0040 14.9925 -6.0192 0.1754 0.7087 -0.6593
0.0036 -14.9925 6.0199 -0.1667 -0.7553 0.5973
26.0023 -1.0012 -6.0070 0.1522 0.5692 0.8179
20.0082 -6.9954 9.0015 -0.4338 0.1001 0.9251
-26.0023 0.0016 6.0084 -0.1460 -0.6187 -0.7798
-20.0069 7.9957 -6.0033 0.2977 -0.0571 -0.9503
-0.0093 -6.0021 -21.9891 0.9899 -0.2495 0.1342

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8045
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.098
_diffrn_reflns_theta_min         2.240
_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 0.999
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00 -13.00   1.00   35.00    --  -16.16 -57.00 120.00   36
  2  ω      0.00  50.00   1.00   35.00    --   16.24  57.00  60.00   50
  3  ω      6.00  55.00   1.00   35.00    --   16.24  57.00 120.00   49
  4  ω    -48.00  35.00   1.00   35.00    --   16.24 -37.00 -90.00   83
;
_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      -0.0043924000
_diffrn_orient_matrix_UB_12      -0.0062722000
_diffrn_orient_matrix_UB_13      -0.0433042000
_diffrn_orient_matrix_UB_21      0.0232943000
_diffrn_orient_matrix_UB_22      0.0495087000
_diffrn_orient_matrix_UB_23      -0.0021791000
_diffrn_orient_matrix_UB_31      0.0309798000
_diffrn_orient_matrix_UB_32      -0.0381126000
_diffrn_orient_matrix_UB_33      0.0042891000
_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                3251
_reflns_number_total             3936
_reflns_odcompleteness_completeness 99.89
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3936
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.042
_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)+(0.0520P)²+1.7054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1188
_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:
 C11(H11), C4(H4), C18(H18), C2(H2), C3(H3), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C)
;
_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 0.59056(6) 0.42303(10) 0.38120(7) 0.0260(3) Uani 1 1 d . . . . .
C6 C 0.60934(6) 0.56269(11) 0.49684(7) 0.0198(3) Uani 1 1 d . . . . .
C1 C 0.58693(6) 0.53964(12) 0.41206(8) 0.0214(3) Uani 1 1 d . . . . .
C7 C 0.62729(6) 0.48595(12) 0.57047(7) 0.0203(3) Uani 1 1 d . . . . .
C12 C 0.65513(7) 0.55900(12) 0.63721(8) 0.0222(3) Uani 1 1 d . . . . .
C8 C 0.61907(7) 0.36372(12) 0.58446(8) 0.0230(3) Uani 1 1 d . . . . .
C5 C 0.62023(6) 0.68051(11) 0.52279(8) 0.0208(3) Uani 1 1 d . . . . .
C11 C 0.67693(7) 0.51380(13) 0.71536(8) 0.0280(3) Uani 1 1 d . . . . .
H11 H 0.695350 0.563686 0.758656 0.034 Uiso 1 1 calc R . . . .
C13 C 0.65659(7) 0.68732(12) 0.61187(8) 0.0224(3) Uani 1 1 d . . . . .
C4 C 0.60106(7) 0.77484(12) 0.47055(8) 0.0258(3) Uani 1 1 d . . . . .
H4 H 0.608538 0.852374 0.489032 0.031 Uiso 1 1 calc R . . . .
C18 C 0.58157(7) 0.28359(12) 0.52184(8) 0.0260(3) Uani 1 1 d . . . . .
H18 H 0.540938 0.313523 0.487148 0.031 Uiso 1 1 calc R . . . .
C2 C 0.56500(7) 0.63568(13) 0.36108(8) 0.0258(3) Uani 1 1 d . . . . .
H2 H 0.546195 0.621955 0.306133 0.031 Uiso 1 1 calc R . . . .
C3 C 0.57037(7) 0.75118(13) 0.38987(8) 0.0277(3) Uani 1 1 d . . . . .
H3 H 0.553287 0.813179 0.354825 0.033 Uiso 1 1 calc R . . . .
C15 C 0.73640(7) 0.72950(13) 0.61606(8) 0.0282(3) Uani 1 1 d . . . . .
H15A H 0.760444 0.729388 0.672182 0.042 Uiso 1 1 calc GR . . . .
H15B H 0.736705 0.808270 0.594230 0.042 Uiso 1 1 calc GR . . . .
H15C H 0.761915 0.677176 0.584392 0.042 Uiso 1 1 calc GR . . . .
C9 C 0.64191(7) 0.32042(13) 0.66412(8) 0.0296(3) Uani 1 1 d . . . . .
H9 H 0.637323 0.239911 0.674059 0.036 Uiso 1 1 calc R . . . .
C10 C 0.67092(8) 0.39326(14) 0.72809(9) 0.0325(3) Uani 1 1 d . . . . .
H10 H 0.686504 0.361446 0.779968 0.039 Uiso 1 1 calc R . . . .
N3 N 0.52640(9) 0.04581(13) 0.39428(11) 0.0620(5) Uani 1 1 d . . . . .
C19 C 0.60020(8) 0.17099(13) 0.50968(9) 0.0318(3) Uani 1 1 d . . . . .
C14 C 0.61578(8) 0.76808(13) 0.66359(8) 0.0311(3) Uani 1 1 d . . . . .
H14A H 0.565131 0.744528 0.657462 0.047 Uiso 1 1 calc GR . . . .
H14B H 0.618813 0.848492 0.645538 0.047 Uiso 1 1 calc GR . . . .
H14C H 0.637725 0.762005 0.720289 0.047 Uiso 1 1 calc GR . . . .
C16 C 0.66647(8) 0.37998(14) 0.38874(9) 0.0337(3) Uani 1 1 d . . . . .
H16A H 0.691172 0.420438 0.349818 0.051 Uiso 1 1 calc GR . . . .
H16B H 0.666203 0.296413 0.377994 0.051 Uiso 1 1 calc GR . . . .
H16C H 0.691722 0.394918 0.443340 0.051 Uiso 1 1 calc GR . . . .
C21 C 0.55848(9) 0.10088(13) 0.44586(11) 0.0400(4) Uani 1 1 d . . . . .
C17 C 0.55194(9) 0.40340(15) 0.29785(9) 0.0382(4) Uani 1 1 d . . . . .
H17A H 0.502650 0.433178 0.293253 0.057 Uiso 1 1 calc GR . . . .
H17B H 0.550566 0.320116 0.286004 0.057 Uiso 1 1 calc GR . . . .
H17C H 0.577211 0.443988 0.259494 0.057 Uiso 1 1 calc GR . . . .
N2 N 0.71332(10) 0.06430(16) 0.58933(12) 0.0774(7) Uani 1 1 d . . . . .
C20 C 0.66364(10) 0.11254(15) 0.55469(11) 0.0459(4) 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 1.4171(17) . ?
N1 C16 1.4671(17) . ?
N1 C17 1.4601(17) . ?
C6 C1 1.4173(17) . ?
C6 C7 1.4854(17) . ?
C6 C5 1.4021(17) . ?
C1 C2 1.3919(19) . ?
C7 C12 1.4052(18) . ?
C7 C8 1.4116(18) . ?
C12 C11 1.3846(18) . ?
C12 C13 1.5095(18) . ?
C8 C18 1.4609(19) . ?
C8 C9 1.4018(18) . ?
C5 C13 1.5160(17) . ?
C5 C4 1.3799(18) . ?
C11 H11 0.9300 . ?
C11 C10 1.384(2) . ?
C13 C15 1.5367(18) . ?
C13 C14 1.5266(18) . ?
C4 H4 0.9300 . ?
C4 C3 1.3860(18) . ?
C18 H18 0.9300 . ?
C18 C19 1.340(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C9 H9 0.9300 . ?
C9 C10 1.377(2) . ?
C10 H10 0.9300 . ?
N3 C21 1.140(2) . ?
C19 C21 1.438(2) . ?
C19 C20 1.440(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N2 C20 1.137(2) . ?

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 C16 112.12(11) . . ?
C1 N1 C17 115.80(11) . . ?
C17 N1 C16 110.10(11) . . ?
C1 C6 C7 133.71(12) . . ?
C5 C6 C1 118.70(11) . . ?
C5 C6 C7 107.56(11) . . ?
N1 C1 C6 120.13(11) . . ?
C2 C1 N1 122.20(11) . . ?
C2 C1 C6 117.60(12) . . ?
C12 C7 C6 107.67(11) . . ?
C12 C7 C8 118.77(11) . . ?
C8 C7 C6 133.51(11) . . ?
C7 C12 C13 111.54(11) . . ?
C11 C12 C7 121.86(13) . . ?
C11 C12 C13 126.60(12) . . ?
C7 C8 C18 122.75(11) . . ?
C9 C8 C7 118.06(12) . . ?
C9 C8 C18 118.92(12) . . ?
C6 C5 C13 111.31(11) . . ?
C4 C5 C6 122.15(12) . . ?
C4 C5 C13 126.52(12) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 C12 119.04(13) . . ?
C10 C11 H11 120.5 . . ?
C12 C13 C5 101.24(10) . . ?
C12 C13 C15 110.15(10) . . ?
C12 C13 C14 112.73(11) . . ?
C5 C13 C15 109.29(10) . . ?
C5 C13 C14 113.02(10) . . ?
C14 C13 C15 110.08(11) . . ?
C5 C4 H4 120.8 . . ?
C5 C4 C3 118.35(13) . . ?
C3 C4 H4 120.8 . . ?
C8 C18 H18 116.9 . . ?
C19 C18 C8 126.15(13) . . ?
C19 C18 H18 116.9 . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.90(12) . . ?
C3 C2 H2 119.1 . . ?
C4 C3 C2 120.40(12) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C9 H9 119.0 . . ?
C10 C9 C8 122.10(13) . . ?
C10 C9 H9 119.0 . . ?
C11 C10 H10 119.9 . . ?
C9 C10 C11 120.13(13) . . ?
C9 C10 H10 119.9 . . ?
C18 C19 C21 120.82(13) . . ?
C18 C19 C20 124.31(13) . . ?
C21 C19 C20 114.81(13) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C21 C19 178.6(2) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C20 C19 178.58(19) . . ?

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 -171.69(12) . . . . ?
C6 C1 C2 C3 5.34(18) . . . . ?
C6 C7 C12 C11 179.84(12) . . . . ?
C6 C7 C12 C13 0.46(13) . . . . ?
C6 C7 C8 C18 -5.4(2) . . . . ?
C6 C7 C8 C9 -179.29(13) . . . . ?
C6 C5 C13 C12 -7.86(13) . . . . ?
C6 C5 C13 C15 108.35(12) . . . . ?
C6 C5 C13 C14 -128.69(12) . . . . ?
C6 C5 C4 C3 -0.28(19) . . . . ?
C1 C6 C7 C12 172.67(13) . . . . ?
C1 C6 C7 C8 -10.2(2) . . . . ?
C1 C6 C5 C13 -169.99(10) . . . . ?
C1 C6 C5 C4 8.37(18) . . . . ?
C1 C2 C3 C4 2.8(2) . . . . ?
C7 C6 C1 N1 -11.6(2) . . . . ?
C7 C6 C1 C2 171.33(12) . . . . ?
C7 C6 C5 C13 8.53(13) . . . . ?
C7 C6 C5 C4 -173.11(11) . . . . ?
C7 C12 C11 C10 -0.2(2) . . . . ?
C7 C12 C13 C5 4.27(13) . . . . ?
C7 C12 C13 C15 -111.31(12) . . . . ?
C7 C12 C13 C14 125.31(12) . . . . ?
C7 C8 C18 C19 143.67(15) . . . . ?
C7 C8 C9 C10 0.7(2) . . . . ?
C12 C7 C8 C18 171.47(12) . . . . ?
C12 C7 C8 C9 -2.44(18) . . . . ?
C12 C11 C10 C9 -1.6(2) . . . . ?
C8 C7 C12 C11 2.23(18) . . . . ?
C8 C7 C12 C13 -177.14(11) . . . . ?
C8 C18 C19 C21 179.75(14) . . . . ?
C8 C18 C19 C20 -3.4(3) . . . . ?
C8 C9 C10 C11 1.3(2) . . . . ?
C5 C6 C1 N1 166.46(11) . . . . ?
C5 C6 C1 C2 -10.63(17) . . . . ?
C5 C6 C7 C12 -5.52(13) . . . . ?
C5 C6 C7 C8 171.58(13) . . . . ?
C5 C4 C3 C2 -5.34(19) . . . . ?
C11 C12 C13 C5 -175.07(12) . . . . ?
C11 C12 C13 C15 69.35(16) . . . . ?
C11 C12 C13 C14 -54.03(17) . . . . ?
C13 C12 C11 C10 179.09(13) . . . . ?
C13 C5 C4 C3 177.82(12) . . . . ?
C4 C5 C13 C12 173.87(12) . . . . ?
C4 C5 C13 C15 -69.92(16) . . . . ?
C4 C5 C13 C14 53.03(17) . . . . ?
C18 C8 C9 C10 -173.43(13) . . . . ?
C9 C8 C18 C19 -42.5(2) . . . . ?
C16 N1 C1 C6 -65.30(15) . . . . ?
C16 N1 C1 C2 111.65(14) . . . . ?
C17 N1 C1 C6 167.21(11) . . . . ?
C17 N1 C1 C2 -15.84(18) . . . . ?

_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 1.020
_oxdiff_exptl_absorpt_empirical_full_min 0.976
####################################################################### 
# 
# 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_jb420abs
_database_code_depnum_ccdc_archive 'CCDC 2069102'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 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        
Cyano-(1,1-dimethyl-5,6-diphenyl-1,2-dihydrobenzo[cd]indol-1-ium-2-yl)-methoxycarbonyl-methanide
_chemical_formula_moiety         'C29 H24 N2 O2'
_chemical_formula_sum            'C29 H24 N2 O2'
_chemical_formula_weight         432.50
_chemical_melting_point          438-441
_chemical_oxdiff_formula         'C29 H24 O2 N2'
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.6932(3)
_cell_length_b                   8.4601(3)
_cell_length_c                   25.0272(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.328(3)
_cell_angle_gamma                90
_cell_volume                     2219.99(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7137
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      30.8370
_cell_measurement_theta_min      3.7160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.734
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
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    brown
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -12 1 0.1194
-2 12 -1 0.1315
15 1 -5 0.2798
-15 -1 5 0.2493
-10 8 -6 0.1558
9 -7 13 0.1679
0 0 -35 0.2625
0 0 35 0.2169
-1 11 11 0.1124
-12 -1 -15 0.1023
12 -1 14 0.1428

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
_exptl_crystal_size_max          0.726
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.258
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
-0.0157 -11.9209 1.3111 0.3692 0.6025 -0.7075
-2.2276 11.7850 -0.6146 -0.3100 -0.5058 0.8050
14.9748 1.1867 -4.6801 -0.4039 -0.6596 -0.6339
-14.9826 -1.1218 4.6754 0.4021 0.6566 0.6381
-10.0509 8.0620 -6.2819 0.2075 -0.1274 0.9699
9.1418 -7.4094 12.9928 -0.3675 0.2254 -0.9023
0.4567 0.0026 -34.7754 0.8515 -0.5216 0.0529
-0.1970 -0.2080 34.6643 -0.8502 0.5208 -0.0772
-1.3605 11.2789 11.4237 -0.6207 -0.3371 0.7079
-11.9987 -0.6010 -15.3657 0.7880 0.2337 0.5696
12.4447 -0.6145 13.7378 -0.7209 -0.2138 -0.6593

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            20457
_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         28.282
_diffrn_reflns_theta_min         3.326
_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 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  49.20   0.30   30.00    --   20.20 -19.00 150.00  334
  2  φ     12.00 106.20   0.30   30.00 -14.74  20.20   0.00    --   314
  3  ω    -49.00  38.00   1.00   30.00    --   20.20 -37.00  30.00   87
  4  ω    -87.00 -28.00   1.00   30.00    --  -20.05 -57.00  30.00   59
  5  ω     -9.00  67.00   1.00   30.00    --   20.20  19.00-150.00   76
;
_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      -0.0320889000
_diffrn_orient_matrix_UB_12      -0.0336716000
_diffrn_orient_matrix_UB_13      -0.0249104000
_diffrn_orient_matrix_UB_21      -0.0356299000
_diffrn_orient_matrix_UB_22      -0.0488996000
_diffrn_orient_matrix_UB_23      0.0145285000
_diffrn_orient_matrix_UB_31      -0.0476901000
_diffrn_orient_matrix_UB_32      0.0591799000
_diffrn_orient_matrix_UB_33      -0.0021427000
_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                4823
_reflns_number_total             5513
_reflns_odcompleteness_completeness 99.73
_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 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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         0.310
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         5513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.026
_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)+(0.0542P)²+0.6186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1067
_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 Ternary CH refined with riding coordinates:
 C25(H25)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C8(H8), C7(H7), C20(H20), C24(H24), C14(H14), C17(H17), C15(H15),
 C16(H16), C3(H3), C2(H2), C21(H21), C23(H23), C22(H22)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), 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
O2 O 0.46074(8) 0.36154(10) 0.85140(3) 0.02791(19) Uani 1 1 d . . . . .
O1 O 0.34490(9) 0.58350(11) 0.83122(3) 0.0362(2) Uani 1 1 d . . . . .
N1 N 0.45682(9) 0.73710(11) 0.71557(4) 0.0242(2) Uani 1 1 d . . . . .
N2 N 0.57961(11) 0.23437(13) 0.74295(4) 0.0365(3) Uani 1 1 d . . . . .
C6 C 0.27695(9) 0.49592(12) 0.54768(4) 0.0200(2) Uani 1 1 d . . . . .
C5 C 0.33563(9) 0.64025(12) 0.57048(4) 0.0187(2) Uani 1 1 d . . . . .
C13 C 0.34487(9) 0.80059(12) 0.48342(4) 0.0194(2) Uani 1 1 d . . . . .
C10 C 0.36892(9) 0.64334(12) 0.62802(4) 0.0195(2) Uani 1 1 d . . . . .
C9 C 0.34938(9) 0.51832(12) 0.66237(4) 0.0206(2) Uani 1 1 d . . . . .
C19 C 0.22292(10) 0.47549(12) 0.48843(4) 0.0216(2) Uani 1 1 d . . . . .
C1 C 0.42274(10) 0.77533(13) 0.65714(4) 0.0213(2) Uani 1 1 d . . . . .
C18 C 0.40740(10) 0.70219(12) 0.45255(4) 0.0218(2) Uani 1 1 d . . . . .
H18 H 0.461355 0.623320 0.469689 0.026 Uiso 1 1 calc R . . . .
C26 C 0.43632(10) 0.46099(13) 0.76334(4) 0.0238(2) Uani 1 1 d . . . . .
C4 C 0.36374(9) 0.78301(12) 0.54369(4) 0.0199(2) Uani 1 1 d . . . . .
C8 C 0.30065(10) 0.37955(13) 0.63988(4) 0.0235(2) Uani 1 1 d . . . . .
H8 H 0.290879 0.292862 0.661536 0.028 Uiso 1 1 calc R . . . .
C7 C 0.26533(10) 0.37163(12) 0.58237(4) 0.0233(2) Uani 1 1 d . . . . .
H7 H 0.232193 0.276823 0.566898 0.028 Uiso 1 1 calc R . . . .
C27 C 0.51510(11) 0.33671(14) 0.75207(4) 0.0260(2) Uani 1 1 d . . . . .
C25 C 0.37662(10) 0.57017(12) 0.72107(4) 0.0219(2) Uani 1 1 d . . . . .
H25 H 0.294754 0.601088 0.729940 0.026 Uiso 1 1 calc R . . . .
C20 C 0.12295(10) 0.57079(14) 0.46260(4) 0.0256(2) Uani 1 1 d . . . . .
H20 H 0.087183 0.644355 0.482791 0.031 Uiso 1 1 calc R . . . .
C24 C 0.27183(11) 0.36195(13) 0.45775(5) 0.0274(2) Uani 1 1 d . . . . .
H24 H 0.335331 0.293350 0.474714 0.033 Uiso 1 1 calc R . . . .
C14 C 0.26584(10) 0.91939(13) 0.45699(4) 0.0239(2) Uani 1 1 d . . . . .
H14 H 0.225398 0.988067 0.477152 0.029 Uiso 1 1 calc R . . . .
C17 C 0.39000(10) 0.72063(14) 0.39645(4) 0.0257(2) Uani 1 1 d . . . . .
H17 H 0.432627 0.654764 0.376234 0.031 Uiso 1 1 calc R . . . .
C15 C 0.24703(11) 0.93596(13) 0.40081(5) 0.0275(2) Uani 1 1 d . . . . .
H15 H 0.192431 1.013870 0.383422 0.033 Uiso 1 1 calc R . . . .
C28 C 0.40908(10) 0.47826(13) 0.81669(4) 0.0241(2) Uani 1 1 d . . . . .
C16 C 0.30918(11) 0.83707(14) 0.37063(4) 0.0273(2) Uani 1 1 d . . . . .
H16 H 0.296714 0.848747 0.333007 0.033 Uiso 1 1 calc R . . . .
C3 C 0.41296(10) 0.91242(13) 0.57474(4) 0.0240(2) Uani 1 1 d . . . . .
H3 H 0.426851 1.004740 0.556594 0.029 Uiso 1 1 calc R . . . .
C2 C 0.44336(11) 0.91275(13) 0.63228(4) 0.0250(2) Uani 1 1 d . . . . .
H2 H 0.475623 1.001967 0.651983 0.030 Uiso 1 1 calc R . . . .
C21 C 0.07624(12) 0.55701(15) 0.40703(5) 0.0321(3) Uani 1 1 d . . . . .
H21 H 0.009126 0.620832 0.390222 0.038 Uiso 1 1 calc R . . . .
C23 C 0.22610(13) 0.35084(14) 0.40193(5) 0.0334(3) Uani 1 1 d . . . . .
H23 H 0.261054 0.277008 0.381554 0.040 Uiso 1 1 calc R . . . .
C29 C 0.43827(12) 0.37449(16) 0.90598(5) 0.0329(3) Uani 1 1 d . . . . .
H29A H 0.348117 0.375005 0.905103 0.049 Uiso 1 1 calc GR . . . .
H29B H 0.475144 0.470917 0.922122 0.049 Uiso 1 1 calc GR . . . .
H29C H 0.476546 0.286200 0.927177 0.049 Uiso 1 1 calc GR . . . .
C22 C 0.12920(13) 0.44859(15) 0.37656(5) 0.0352(3) Uani 1 1 d . . . . .
H22 H 0.099610 0.441652 0.339120 0.042 Uiso 1 1 calc R . . . .
C11 C 0.41795(14) 0.86240(14) 0.75085(5) 0.0348(3) Uani 1 1 d . . . . .
H11A H 0.465146 0.957307 0.747652 0.052 Uiso 1 1 calc GR . . . .
H11B H 0.435291 0.827535 0.788074 0.052 Uiso 1 1 calc GR . . . .
H11C H 0.328383 0.883082 0.739541 0.052 Uiso 1 1 calc GR . . . .
C12 C 0.59710(11) 0.70835(19) 0.73080(5) 0.0407(3) Uani 1 1 d . . . . .
H12A H 0.620839 0.627696 0.707711 0.061 Uiso 1 1 calc GR . . . .
H12B H 0.618607 0.674675 0.768108 0.061 Uiso 1 1 calc GR . . . .
H12C H 0.642025 0.804202 0.726367 0.061 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
O2 C28 1.3587(13) . ?
O2 C29 1.4369(13) . ?
O1 C28 1.2223(13) . ?
N1 C1 1.4720(12) . ?
N1 C25 1.6719(14) . ?
N1 C11 1.4899(15) . ?
N1 C12 1.4932(15) . ?
N2 C27 1.1574(15) . ?
C6 C5 1.4386(14) . ?
C6 C19 1.4921(14) . ?
C6 C7 1.3846(14) . ?
C5 C10 1.4141(13) . ?
C5 C4 1.4415(13) . ?
C13 C18 1.3928(14) . ?
C13 C4 1.4895(13) . ?
C13 C14 1.3937(14) . ?
C10 C9 1.4041(14) . ?
C10 C1 1.3944(14) . ?
C9 C8 1.3607(15) . ?
C9 C25 1.5058(14) . ?
C19 C20 1.3926(15) . ?
C19 C24 1.3940(15) . ?
C1 C2 1.3568(15) . ?
C18 H18 0.9300 . ?
C18 C17 1.3883(14) . ?
C26 C27 1.4100(15) . ?
C26 C25 1.4543(14) . ?
C26 C28 1.4289(14) . ?
C4 C3 1.3853(15) . ?
C8 H8 0.9300 . ?
C8 C7 1.4160(15) . ?
C7 H7 0.9300 . ?
C25 H25 0.9800 . ?
C20 H20 0.9300 . ?
C20 C21 1.3872(15) . ?
C24 H24 0.9300 . ?
C24 C23 1.3897(16) . ?
C14 H14 0.9300 . ?
C14 C15 1.3877(15) . ?
C17 H17 0.9300 . ?
C17 C16 1.3841(17) . ?
C15 H15 0.9300 . ?
C15 C16 1.3818(17) . ?
C16 H16 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.4127(15) . ?
C2 H2 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.3833(19) . ?
C23 H23 0.9300 . ?
C23 C22 1.3792(19) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C22 H22 0.9300 . ?
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
C28 O2 C29 115.43(9) . . ?
C1 N1 C25 103.67(7) . . ?
C1 N1 C11 112.89(9) . . ?
C1 N1 C12 109.24(9) . . ?
C11 N1 C25 110.18(8) . . ?
C11 N1 C12 110.35(10) . . ?
C12 N1 C25 110.32(9) . . ?
C5 C6 C19 123.10(9) . . ?
C7 C6 C5 118.80(9) . . ?
C7 C6 C19 118.05(9) . . ?
C6 C5 C4 129.88(9) . . ?
C10 C5 C6 114.99(9) . . ?
C10 C5 C4 115.12(9) . . ?
C18 C13 C4 121.18(9) . . ?
C18 C13 C14 118.70(9) . . ?
C14 C13 C4 120.10(9) . . ?
C9 C10 C5 124.85(9) . . ?
C1 C10 C5 122.85(9) . . ?
C1 C10 C9 112.28(9) . . ?
C10 C9 C25 110.75(9) . . ?
C8 C9 C10 119.18(9) . . ?
C8 C9 C25 129.78(9) . . ?
C20 C19 C6 120.42(10) . . ?
C20 C19 C24 118.69(10) . . ?
C24 C19 C6 120.89(10) . . ?
C10 C1 N1 109.84(9) . . ?
C2 C1 N1 127.80(9) . . ?
C2 C1 C10 122.29(9) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.68(10) . . ?
C17 C18 H18 119.7 . . ?
C27 C26 C25 121.49(9) . . ?
C27 C26 C28 120.17(9) . . ?
C28 C26 C25 118.29(10) . . ?
C5 C4 C13 123.76(9) . . ?
C3 C4 C5 119.48(9) . . ?
C3 C4 C13 116.76(9) . . ?
C9 C8 H8 121.1 . . ?
C9 C8 C7 117.73(9) . . ?
C7 C8 H8 121.1 . . ?
C6 C7 C8 124.22(10) . . ?
C6 C7 H7 117.9 . . ?
C8 C7 H7 117.9 . . ?
N2 C27 C26 179.77(13) . . ?
N1 C25 H25 106.8 . . ?
C9 C25 N1 99.78(7) . . ?
C9 C25 H25 106.8 . . ?
C26 C25 N1 115.94(8) . . ?
C26 C25 C9 119.86(9) . . ?
C26 C25 H25 106.8 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.61(11) . . ?
C21 C20 H20 119.7 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.28(11) . . ?
C23 C24 H24 119.9 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.49(10) . . ?
C15 C14 H14 119.8 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 119.97(10) . . ?
C16 C17 H17 120.0 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.21(10) . . ?
C16 C15 H15 119.9 . . ?
O2 C28 C26 113.03(9) . . ?
O1 C28 O2 121.38(10) . . ?
O1 C28 C26 125.59(10) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 119.93(10) . . ?
C15 C16 H16 120.0 . . ?
C4 C3 H3 118.0 . . ?
C4 C3 C2 124.02(10) . . ?
C2 C3 H3 118.0 . . ?
C1 C2 C3 116.10(10) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 H2 121.9 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.18(11) . . ?
C22 C21 H21 119.9 . . ?
C24 C23 H23 119.8 . . ?
C22 C23 C24 120.43(11) . . ?
C22 C23 H23 119.8 . . ?
O2 C29 H29A 109.5 . . ?
O2 C29 H29B 109.5 . . ?
O2 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.71(11) . . ?
C23 C22 H22 120.1 . . ?
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 173.61(10) . . . . ?
C6 C5 C10 C9 0.46(15) . . . . ?
C6 C5 C10 C1 -177.83(9) . . . . ?
C6 C5 C4 C13 -5.63(17) . . . . ?
C6 C5 C4 C3 175.35(10) . . . . ?
C6 C19 C20 C21 177.10(10) . . . . ?
C6 C19 C24 C23 -175.92(10) . . . . ?
C5 C6 C19 C20 -61.15(14) . . . . ?
C5 C6 C19 C24 118.34(11) . . . . ?
C5 C6 C7 C8 4.01(16) . . . . ?
C5 C10 C9 C8 3.36(16) . . . . ?
C5 C10 C9 C25 -171.13(9) . . . . ?
C5 C10 C1 N1 -175.00(9) . . . . ?
C5 C10 C1 C2 2.19(16) . . . . ?
C5 C4 C3 C2 2.78(17) . . . . ?
C13 C18 C17 C16 -0.43(16) . . . . ?
C13 C4 C3 C2 -176.31(10) . . . . ?
C13 C14 C15 C16 -1.63(17) . . . . ?
C10 C5 C4 C13 175.52(9) . . . . ?
C10 C5 C4 C3 -3.50(14) . . . . ?
C10 C9 C8 C7 -3.44(15) . . . . ?
C10 C9 C25 N1 -15.70(10) . . . . ?
C10 C9 C25 C26 -143.34(10) . . . . ?
C10 C1 C2 C3 -3.03(16) . . . . ?
C9 C10 C1 N1 6.52(12) . . . . ?
C9 C10 C1 C2 -176.29(10) . . . . ?
C9 C8 C7 C6 -0.15(16) . . . . ?
C19 C6 C5 C10 173.50(9) . . . . ?
C19 C6 C5 C4 -5.35(16) . . . . ?
C19 C6 C7 C8 -173.57(10) . . . . ?
C19 C20 C21 C22 -0.36(17) . . . . ?
C19 C24 C23 C22 -2.01(18) . . . . ?
C1 N1 C25 C9 18.48(9) . . . . ?
C1 N1 C25 C26 148.70(9) . . . . ?
C1 C10 C9 C8 -178.19(10) . . . . ?
C1 C10 C9 C25 7.32(12) . . . . ?
C18 C13 C4 C5 -59.24(14) . . . . ?
C18 C13 C4 C3 119.80(11) . . . . ?
C18 C13 C14 C15 1.90(16) . . . . ?
C18 C17 C16 C15 0.73(16) . . . . ?
C4 C5 C10 C9 179.49(9) . . . . ?
C4 C5 C10 C1 1.20(14) . . . . ?
C4 C13 C18 C17 -179.39(9) . . . . ?
C4 C13 C14 C15 -179.56(10) . . . . ?
C4 C3 C2 C1 0.57(17) . . . . ?
C8 C9 C25 N1 170.57(11) . . . . ?
C8 C9 C25 C26 42.93(16) . . . . ?
C7 C6 C5 C10 -3.95(14) . . . . ?
C7 C6 C5 C4 177.20(10) . . . . ?
C7 C6 C19 C20 116.32(11) . . . . ?
C7 C6 C19 C24 -64.19(14) . . . . ?
C27 C26 C25 N1 -93.64(12) . . . . ?
C27 C26 C25 C9 26.16(16) . . . . ?
C27 C26 C28 O2 -3.04(16) . . . . ?
C27 C26 C28 O1 178.06(12) . . . . ?
C25 N1 C1 C10 -15.79(11) . . . . ?
C25 N1 C1 C2 167.22(11) . . . . ?
C25 C9 C8 C7 169.85(10) . . . . ?
C25 C26 C28 O2 174.43(10) . . . . ?
C25 C26 C28 O1 -4.48(18) . . . . ?
C20 C19 C24 C23 3.58(16) . . . . ?
C20 C21 C22 C23 1.98(18) . . . . ?
C24 C19 C20 C21 -2.40(16) . . . . ?
C24 C23 C22 C21 -0.80(18) . . . . ?
C14 C13 C18 C17 -0.88(15) . . . . ?
C14 C13 C4 C5 122.26(11) . . . . ?
C14 C13 C4 C3 -58.70(13) . . . . ?
C14 C15 C16 C17 0.30(17) . . . . ?
C28 C26 C25 N1 88.93(12) . . . . ?
C28 C26 C25 C9 -151.27(10) . . . . ?
C29 O2 C28 O1 -2.11(16) . . . . ?
C29 O2 C28 C26 178.94(10) . . . . ?
C11 N1 C1 C10 -135.00(10) . . . . ?
C11 N1 C1 C2 48.01(15) . . . . ?
C11 N1 C25 C9 139.54(9) . . . . ?
C11 N1 C25 C26 -90.25(11) . . . . ?
C12 N1 C1 C10 101.82(11) . . . . ?
C12 N1 C1 C2 -75.17(14) . . . . ?
C12 N1 C25 C9 -98.38(10) . . . . ?
C12 N1 C25 C26 31.84(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 1.165
_oxdiff_exptl_absorpt_empirical_full_min 0.838
####################################################################### 
# 
# 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_jb412abs
_database_code_depnum_ccdc_archive 'CCDC 2069100'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
1-Dimethylamino-4,5-diphenylnaphthalene
;
_chemical_formula_moiety         'C24 H21 N'
_chemical_formula_sum            'C24 H21 N'
_chemical_formula_weight         323.42
_chemical_melting_point          236-237
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.0584(7)
_cell_length_b                   9.7183(2)
_cell_length_c                   16.5596(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.142(3)
_cell_angle_gamma                90
_cell_volume                     3504.78(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6450
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.122
_cell_measurement_theta_min      3.503
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_min  0.93259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            35872
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.277
_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2558
_reflns_number_total             3568
_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    ?
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    SHELXS
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3568
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.030
_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)+(0.0454P)²+1.2734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1137
_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), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 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 0.41805(6) 0.39271(13) 0.09355(8) 0.0345(3) Uani 1 1 d . . . . .
C1 C 0.35654(7) 0.39906(15) 0.10945(9) 0.0309(4) Uani 1 1 d . . . . .
C2 C 0.30672(8) 0.40784(16) 0.04914(10) 0.0342(4) Uani 1 1 d . . . . .
H2 H 0.312289 0.415464 -0.005179 0.041 Uiso 1 1 calc R . . . .
C3 C 0.24733(7) 0.40542(16) 0.06868(9) 0.0337(4) Uani 1 1 d . . . . .
H3 H 0.214296 0.410239 0.026213 0.040 Uiso 1 1 calc R . . . .
C4 C 0.23530(7) 0.39633(15) 0.14721(9) 0.0290(4) Uani 1 1 d . . . . .
C5 C 0.28625(7) 0.39187(14) 0.21339(9) 0.0285(4) Uani 1 1 d . . . . .
C6 C 0.28067(7) 0.38563(15) 0.29900(9) 0.0306(4) Uani 1 1 d . . . . .
C7 C 0.33258(8) 0.36306(16) 0.35579(10) 0.0356(4) Uani 1 1 d . . . . .
H7 H 0.328601 0.357650 0.410775 0.043 Uiso 1 1 calc R . . . .
C8 C 0.39059(8) 0.34808(17) 0.33426(10) 0.0375(4) Uani 1 1 d . . . . .
H8 H 0.424167 0.327992 0.374000 0.045 Uiso 1 1 calc R . . . .
C9 C 0.39794(8) 0.36290(16) 0.25507(10) 0.0349(4) Uani 1 1 d . . . . .
H9 H 0.437073 0.356704 0.241161 0.042 Uiso 1 1 calc R . . . .
C10 C 0.34704(7) 0.38767(15) 0.19309(9) 0.0299(4) Uani 1 1 d . . . . .
C11 C 0.45214(8) 0.52123(18) 0.11093(11) 0.0430(4) Uani 1 1 d . . . . .
H11A H 0.438243 0.587267 0.068939 0.065 Uiso 1 1 calc GR . . . .
H11B H 0.495166 0.504244 0.112353 0.065 Uiso 1 1 calc GR . . . .
H11C H 0.445372 0.556526 0.162908 0.065 Uiso 1 1 calc GR . . . .
C12 C 0.42523(8) 0.3411(2) 0.01311(10) 0.0448(5) Uani 1 1 d . . . . .
H12A H 0.401767 0.258108 0.001878 0.067 Uiso 1 1 calc GR . . . .
H12B H 0.467790 0.322040 0.011969 0.067 Uiso 1 1 calc GR . . . .
H12C H 0.410859 0.408937 -0.027567 0.067 Uiso 1 1 calc GR . . . .
C13 C 0.16951(7) 0.38084(15) 0.15625(9) 0.0289(4) Uani 1 1 d . . . . .
C14 C 0.12712(8) 0.48178(17) 0.12621(10) 0.0346(4) Uani 1 1 d . . . . .
H14 H 0.140555 0.560961 0.102936 0.041 Uiso 1 1 calc R . . . .
C15 C 0.06548(8) 0.46647(18) 0.13034(10) 0.0401(4) Uani 1 1 d . . . . .
H15 H 0.037856 0.535332 0.110307 0.048 Uiso 1 1 calc R . . . .
C16 C 0.04481(8) 0.34922(19) 0.16412(10) 0.0406(4) Uani 1 1 d . . . . .
H16 H 0.003362 0.339053 0.167487 0.049 Uiso 1 1 calc R . . . .
C17 C 0.08607(8) 0.24707(18) 0.19291(10) 0.0379(4) Uani 1 1 d . . . . .
H17 H 0.072203 0.167361 0.215134 0.046 Uiso 1 1 calc R . . . .
C18 C 0.14782(7) 0.26217(16) 0.18901(9) 0.0321(4) Uani 1 1 d . . . . .
H18 H 0.175130 0.192381 0.208457 0.038 Uiso 1 1 calc R . . . .
C19 C 0.22283(7) 0.40476(16) 0.33375(9) 0.0310(4) Uani 1 1 d . . . . .
C20 C 0.18695(8) 0.52243(16) 0.32015(9) 0.0329(4) Uani 1 1 d . . . . .
H20 H 0.197697 0.590796 0.285755 0.039 Uiso 1 1 calc R . . . .
C21 C 0.13542(8) 0.53930(18) 0.35708(10) 0.0373(4) Uani 1 1 d . . . . .
H21 H 0.111562 0.618163 0.346818 0.045 Uiso 1 1 calc R . . . .
C22 C 0.11927(8) 0.4396(2) 0.40906(10) 0.0413(4) Uani 1 1 d . . . . .
H22 H 0.084658 0.451103 0.433927 0.050 Uiso 1 1 calc R . . . .
C23 C 0.15483(8) 0.32295(19) 0.42387(10) 0.0420(4) Uani 1 1 d . . . . .
H23 H 0.144233 0.255838 0.459158 0.050 Uiso 1 1 calc R . . . .
C24 C 0.20600(8) 0.30492(18) 0.38675(9) 0.0373(4) Uani 1 1 d . . . . .
H24 H 0.229522 0.225574 0.397097 0.045 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.424(2) . ?
N1 C11 1.463(2) . ?
N1 C12 1.455(2) . ?
C1 C2 1.365(2) . ?
C1 C10 1.438(2) . ?
C2 C3 1.399(2) . ?
C3 C4 1.371(2) . ?
C4 C5 1.440(2) . ?
C4 C13 1.490(2) . ?
C5 C6 1.444(2) . ?
C5 C10 1.434(2) . ?
C6 C7 1.379(2) . ?
C6 C19 1.492(2) . ?
C7 C8 1.389(2) . ?
C8 C9 1.354(2) . ?
C9 C10 1.416(2) . ?
C13 C14 1.391(2) . ?
C13 C18 1.391(2) . ?
C14 C15 1.380(2) . ?
C15 C16 1.378(2) . ?
C16 C17 1.380(2) . ?
C17 C18 1.382(2) . ?
C19 C20 1.389(2) . ?
C19 C24 1.398(2) . ?
C20 C21 1.383(2) . ?
C21 C22 1.380(2) . ?
C22 C23 1.378(3) . ?
C23 C24 1.380(2) . ?

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 113.69(13) . . ?
C1 N1 C12 115.44(13) . . ?
C12 N1 C11 110.33(13) . . ?
N1 C1 C10 117.65(14) . . ?
C2 C1 N1 123.19(14) . . ?
C2 C1 C10 119.07(15) . . ?
C1 C2 C3 120.30(15) . . ?
C4 C3 C2 123.38(15) . . ?
C3 C4 C5 118.60(14) . . ?
C3 C4 C13 116.12(13) . . ?
C5 C4 C13 125.11(13) . . ?
C4 C5 C6 124.79(14) . . ?
C10 C5 C4 117.91(13) . . ?
C10 C5 C6 117.26(14) . . ?
C5 C6 C19 125.80(14) . . ?
C7 C6 C5 119.03(15) . . ?
C7 C6 C19 115.16(14) . . ?
C6 C7 C8 122.72(15) . . ?
C9 C8 C7 119.62(15) . . ?
C8 C9 C10 121.10(16) . . ?
C5 C10 C1 120.58(14) . . ?
C9 C10 C1 119.41(15) . . ?
C9 C10 C5 119.87(14) . . ?
C14 C13 C4 120.19(14) . . ?
C18 C13 C4 121.57(14) . . ?
C18 C13 C14 118.07(15) . . ?
C15 C14 C13 121.17(16) . . ?
C16 C15 C14 120.07(16) . . ?
C15 C16 C17 119.50(16) . . ?
C16 C17 C18 120.58(16) . . ?
C17 C18 C13 120.58(15) . . ?
C20 C19 C6 122.70(14) . . ?
C20 C19 C24 118.17(15) . . ?
C24 C19 C6 118.97(14) . . ?
C21 C20 C19 120.87(15) . . ?
C22 C21 C20 120.29(17) . . ?
C23 C22 C21 119.51(17) . . ?
C22 C23 C24 120.53(16) . . ?
C23 C24 C19 120.63(16) . . ?

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 176.16(14) . . . . ?
N1 C1 C10 C5 -179.39(13) . . . . ?
N1 C1 C10 C9 -3.6(2) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C2 C1 C10 C5 -2.9(2) . . . . ?
C2 C1 C10 C9 172.90(14) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C2 C3 C4 C13 -174.07(14) . . . . ?
C3 C4 C5 C6 178.46(14) . . . . ?
C3 C4 C5 C10 -4.2(2) . . . . ?
C3 C4 C13 C14 -60.21(19) . . . . ?
C3 C4 C13 C18 115.00(16) . . . . ?
C4 C5 C6 C7 171.29(14) . . . . ?
C4 C5 C6 C19 -10.2(2) . . . . ?
C4 C5 C10 C1 5.0(2) . . . . ?
C4 C5 C10 C9 -170.73(13) . . . . ?
C4 C13 C14 C15 176.81(14) . . . . ?
C4 C13 C18 C17 -176.62(14) . . . . ?
C5 C4 C13 C14 124.73(16) . . . . ?
C5 C4 C13 C18 -60.1(2) . . . . ?
C5 C6 C7 C8 1.0(2) . . . . ?
C5 C6 C19 C20 -56.7(2) . . . . ?
C5 C6 C19 C24 127.83(16) . . . . ?
C6 C5 C10 C1 -177.45(13) . . . . ?
C6 C5 C10 C9 6.8(2) . . . . ?
C6 C7 C8 C9 3.5(2) . . . . ?
C6 C19 C20 C21 -176.48(14) . . . . ?
C6 C19 C24 C23 176.14(14) . . . . ?
C7 C6 C19 C20 121.86(16) . . . . ?
C7 C6 C19 C24 -53.60(19) . . . . ?
C7 C8 C9 C10 -2.7(2) . . . . ?
C8 C9 C10 C1 -178.31(15) . . . . ?
C8 C9 C10 C5 -2.5(2) . . . . ?
C10 C1 C2 C3 -0.1(2) . . . . ?
C10 C5 C6 C7 -6.1(2) . . . . ?
C10 C5 C6 C19 172.47(14) . . . . ?
C11 N1 C1 C2 105.10(18) . . . . ?
C11 N1 C1 C10 -78.54(18) . . . . ?
C12 N1 C1 C2 -23.9(2) . . . . ?
C12 N1 C1 C10 152.49(14) . . . . ?
C13 C4 C5 C6 -6.6(2) . . . . ?
C13 C4 C5 C10 170.75(13) . . . . ?
C13 C14 C15 C16 -0.5(2) . . . . ?
C14 C13 C18 C17 -1.3(2) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C13 0.2(2) . . . . ?
C18 C13 C14 C15 1.4(2) . . . . ?
C19 C6 C7 C8 -177.65(14) . . . . ?
C19 C20 C21 C22 0.8(2) . . . . ?
C20 C19 C24 C23 0.5(2) . . . . ?
C20 C21 C22 C23 -0.1(2) . . . . ?
C21 C22 C23 C24 -0.4(2) . . . . ?
C22 C23 C24 C19 0.2(2) . . . . ?
C24 C19 C20 C21 -1.0(2) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
####################################################################### 
# 
# 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_jb426abs
_database_code_depnum_ccdc_archive 'CCDC 2069104'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 downloaded from the CCDC.
;
_audit_creation_date             2019-07-11
_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        
;
N,N-Bis(4,5-diphenyl-8-dimethylaminonaphth-1-methylidene)-1,2-ethanediamine,
;
_chemical_formula_moiety         'C52 H46 N4'
_chemical_formula_sum            'C52 H46 N4'
_chemical_formula_weight         726.93
_chemical_melting_point          491-494
_chemical_oxdiff_formula         'C26 H23 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.8042(2)
_cell_length_b                   15.4073(4)
_cell_length_c                   52.7317(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7965.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5336
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      70.9420
_cell_measurement_theta_min      4.7890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.893
_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    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3088
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 7 -6 0.0704
5 -4 -16 0.0956
2 3 -30 0.0905
-2 -4 30 0.0836
-1 -1 -34 0.0538
0 0 34 0.0381
4 7 0 0.0880
-4 -7 -1 0.1239
3 -8 -10 0.0830

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/hexane'
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.107
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
-4.0035 6.9944 -6.0125 -0.9148 0.1977 -0.1967
4.9999 -3.9963 -15.9869 0.8275 -0.1894 -0.5241
1.9957 2.9981 -29.9972 0.0225 -0.0311 -0.9770
-1.9948 -3.9987 29.9976 0.0298 -0.0470 1.0113
-0.9988 -1.0112 -34.0024 -0.1790 -0.5988 -0.7943
0.0003 0.0086 34.0005 0.0983 0.4534 0.8782
3.9910 7.0120 0.0061 0.1661 0.8160 -0.4385
-3.9911 -7.0122 -1.0061 -0.1690 -0.8294 0.4126
3.0049 -8.0010 -9.9896 0.7879 -0.5564 -0.1327

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       64
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            20439
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.131
_diffrn_reflns_theta_min         4.812
_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 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     10.00 104.00   1.00   30.00    --   36.58  77.00 120.00   94
  2  ω    -31.00  53.00   1.00   30.00    --   36.58 -57.00 150.00   84
  3  ω     18.00  90.00   1.00   30.00    --   36.58-125.00 -30.00   72
  4  ω     17.00  71.00   1.00   30.00    --   36.58  37.00 120.00   54
  5  ω     26.00  52.00   1.00   30.00    --   36.58-125.00 -60.00   26
  6  ω    108.00 150.00   1.00  120.00    --  108.00 111.00  60.00   42
  7  ω     40.00  92.00   1.00  120.00    --  108.00-111.00-180.00   52
  8  ω     71.00 100.00   1.00  120.00    --  108.00-111.00  60.00   29
  9  ω     52.00 112.00   1.00  120.00    --  108.00-111.00 -30.00   60
 10  ω     70.00 178.00   1.00  120.00    --  108.00  15.00-150.00  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      0.1331383000
_diffrn_orient_matrix_UB_12      -0.0520931000
_diffrn_orient_matrix_UB_13      0.0029021000
_diffrn_orient_matrix_UB_21      0.0671516000
_diffrn_orient_matrix_UB_22      0.0781423000
_diffrn_orient_matrix_UB_23      0.0133146000
_diffrn_orient_matrix_UB_31      -0.0496186000
_diffrn_orient_matrix_UB_32      -0.0343106000
_diffrn_orient_matrix_UB_33      0.0258391000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5584
_reflns_number_total             7645
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (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         0.211
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7645
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.024
_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)+(0.0577P)²+1.2552P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1423
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C27(H27A,H27B)
2.b 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), C28(H28),
  C32(H32), C33(H33), C37(H37), C38(H38), C42(H42), C43(H43), C44(H44),
 C45(H45), C46(H46), C48(H48), C49(H49), C50(H50), C51(H51), C52(H52)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C39(H39A,H39B,H39C), C40(H40A,H40B,
 H40C)
;
_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
N1 N 0.89928(17) 0.68808(12) 0.51567(3) 0.0371(4) Uani 1 1 d . . . . .
N2 N 0.71815(19) 0.49272(13) 0.50190(3) 0.0402(4) Uani 1 1 d . . . . .
N3 N 0.68070(18) 0.50170(13) 0.43189(3) 0.0407(4) Uani 1 1 d . . . . .
N4 N 0.59116(17) 0.28225(12) 0.41226(3) 0.0354(4) Uani 1 1 d . . . . .
C1 C 0.90365(19) 0.68916(14) 0.54265(4) 0.0330(4) Uani 1 1 d . . . . .
C2 C 0.9578(2) 0.75719(14) 0.55591(4) 0.0385(5) Uani 1 1 d . . . . .
H2 H 0.995888 0.803810 0.547223 0.046 Uiso 1 1 calc R . . . .
C3 C 0.9564(2) 0.75720(14) 0.58247(4) 0.0374(5) Uani 1 1 d . . . . .
H3 H 0.987237 0.806240 0.591006 0.045 Uiso 1 1 calc R . . . .
C4 C 0.91128(18) 0.68754(13) 0.59638(4) 0.0313(4) Uani 1 1 d . . . . .
C5 C 0.86540(18) 0.61056(13) 0.58314(4) 0.0301(4) Uani 1 1 d . . . . .
C6 C 0.83218(19) 0.52981(13) 0.59540(4) 0.0325(4) Uani 1 1 d . . . . .
C7 C 0.7731(2) 0.46422(15) 0.58139(4) 0.0407(5) Uani 1 1 d . . . . .
H7 H 0.754392 0.411467 0.589229 0.049 Uiso 1 1 calc R . . . .
C8 C 0.7406(2) 0.47462(15) 0.55588(4) 0.0427(5) Uani 1 1 d . . . . .
H8 H 0.694044 0.430674 0.547433 0.051 Uiso 1 1 calc R . . . .
C9 C 0.7758(2) 0.54821(14) 0.54306(4) 0.0343(4) Uani 1 1 d . . . . .
C10 C 0.84869(19) 0.61592(13) 0.55600(4) 0.0319(4) Uani 1 1 d . . . . .
C11 C 1.0018(2) 0.63103(17) 0.50427(4) 0.0462(6) Uani 1 1 d . . . . .
H11A H 1.090844 0.655584 0.506677 0.069 Uiso 1 1 calc GR . . . .
H11B H 0.983891 0.625106 0.486451 0.069 Uiso 1 1 calc GR . . . .
H11C H 0.997840 0.575000 0.512195 0.069 Uiso 1 1 calc GR . . . .
C12 C 0.8975(3) 0.77236(16) 0.50327(4) 0.0539(6) Uani 1 1 d . . . . .
H12A H 0.832354 0.809284 0.511532 0.081 Uiso 1 1 calc GR . . . .
H12B H 0.872602 0.765292 0.485791 0.081 Uiso 1 1 calc GR . . . .
H12C H 0.986485 0.798155 0.504319 0.081 Uiso 1 1 calc GR . . . .
C13 C 0.90098(19) 0.70173(12) 0.62431(4) 0.0303(4) Uani 1 1 d . . . . .
C14 C 1.0135(2) 0.73000(13) 0.63815(4) 0.0333(4) Uani 1 1 d . . . . .
H14 H 1.097151 0.736530 0.630072 0.040 Uiso 1 1 calc R . . . .
C15 C 1.0026(2) 0.74847(13) 0.66368(4) 0.0373(5) Uani 1 1 d . . . . .
H15 H 1.079127 0.766122 0.672730 0.045 Uiso 1 1 calc R . . . .
C16 C 0.8781(2) 0.74080(14) 0.67583(4) 0.0408(5) Uani 1 1 d . . . . .
H16 H 0.870738 0.753275 0.693033 0.049 Uiso 1 1 calc R . . . .
C17 C 0.7649(2) 0.71451(14) 0.66226(4) 0.0407(5) Uani 1 1 d . . . . .
H17 H 0.680907 0.710039 0.670359 0.049 Uiso 1 1 calc R . . . .
C18 C 0.7753(2) 0.69479(13) 0.63679(4) 0.0342(4) Uani 1 1 d . . . . .
H18 H 0.698472 0.676825 0.627874 0.041 Uiso 1 1 calc R . . . .
C19 C 0.86135(19) 0.50903(13) 0.62243(4) 0.0311(4) Uani 1 1 d . . . . .
C20 C 0.9906(2) 0.52103(13) 0.63289(4) 0.0343(4) Uani 1 1 d . . . . .
H20 H 1.060534 0.543722 0.622990 0.041 Uiso 1 1 calc R . . . .
C21 C 1.0150(2) 0.49943(14) 0.65780(4) 0.0424(5) Uani 1 1 d . . . . .
H21 H 1.101035 0.508820 0.664705 0.051 Uiso 1 1 calc R . . . .
C22 C 0.9133(3) 0.46396(15) 0.67265(4) 0.0484(6) Uani 1 1 d . . . . .
H22 H 0.930212 0.450388 0.689548 0.058 Uiso 1 1 calc R . . . .
C23 C 0.7861(3) 0.44876(15) 0.66226(4) 0.0469(6) Uani 1 1 d . . . . .
H23 H 0.718132 0.423296 0.672042 0.056 Uiso 1 1 calc R . . . .
C24 C 0.7596(2) 0.47126(14) 0.63737(4) 0.0384(5) Uani 1 1 d . . . . .
H24 H 0.673656 0.461209 0.630521 0.046 Uiso 1 1 calc R . . . .
C25 C 0.7206(2) 0.55679(14) 0.51695(4) 0.0358(4) Uani 1 1 d . . . . .
H25 H 0.687201 0.610185 0.511547 0.043 Uiso 1 1 calc R . . . .
C26 C 0.6499(2) 0.50468(16) 0.47769(4) 0.0445(5) Uani 1 1 d . . . . .
H26A H 0.609749 0.562170 0.476989 0.053 Uiso 1 1 calc R . . . .
H26B H 0.577161 0.462402 0.475959 0.053 Uiso 1 1 calc R . . . .
C27 C 0.7502(2) 0.49399(16) 0.45625(4) 0.0441(5) Uani 1 1 d . . . . .
H27A H 0.820517 0.538096 0.457516 0.053 Uiso 1 1 calc R . . . .
H27B H 0.793691 0.437583 0.457450 0.053 Uiso 1 1 calc R . . . .
C28 C 0.7045(2) 0.44221(14) 0.41596(4) 0.0354(4) Uani 1 1 d . . . . .
H28 H 0.755759 0.394238 0.420832 0.043 Uiso 1 1 calc R . . . .
C29 C 0.65216(19) 0.44775(13) 0.38969(3) 0.0309(4) Uani 1 1 d . . . . .
C30 C 0.62348(18) 0.37272(13) 0.37446(3) 0.0282(4) Uani 1 1 d . . . . .
C31 C 0.60290(18) 0.28829(13) 0.38550(3) 0.0304(4) Uani 1 1 d . . . . .
C32 C 0.5957(2) 0.21707(13) 0.37005(4) 0.0337(4) Uani 1 1 d . . . . .
H32 H 0.580579 0.162509 0.377049 0.040 Uiso 1 1 calc R . . . .
C33 C 0.6109(2) 0.22578(13) 0.34381(4) 0.0326(4) Uani 1 1 d . . . . .
H33 H 0.614716 0.175894 0.333906 0.039 Uiso 1 1 calc R . . . .
C34 C 0.62043(18) 0.30496(12) 0.33212(3) 0.0286(4) Uani 1 1 d . . . . .
C35 C 0.61548(18) 0.38223(12) 0.34740(3) 0.0278(4) Uani 1 1 d . . . . .
C36 C 0.60521(19) 0.46852(13) 0.33711(4) 0.0297(4) Uani 1 1 d . . . . .
C37 C 0.6203(2) 0.53828(13) 0.35303(4) 0.0347(4) Uani 1 1 d . . . . .
H37 H 0.610901 0.593972 0.346463 0.042 Uiso 1 1 calc R . . . .
C38 C 0.6493(2) 0.52835(13) 0.37864(4) 0.0351(4) Uani 1 1 d . . . . .
H38 H 0.667055 0.577168 0.388473 0.042 Uiso 1 1 calc R . . . .
C39 C 0.4644(2) 0.31677(15) 0.42275(4) 0.0410(5) Uani 1 1 d . . . . .
H39A H 0.443416 0.371098 0.414740 0.062 Uiso 1 1 calc GR . . . .
H39B H 0.474901 0.325542 0.440671 0.062 Uiso 1 1 calc GR . . . .
H39C H 0.391680 0.276358 0.419745 0.062 Uiso 1 1 calc GR . . . .
C40 C 0.6238(3) 0.19825(16) 0.42338(4) 0.0509(6) Uani 1 1 d . . . . .
H40A H 0.554014 0.157162 0.419045 0.076 Uiso 1 1 calc GR . . . .
H40B H 0.629035 0.203790 0.441488 0.076 Uiso 1 1 calc GR . . . .
H40C H 0.709962 0.178451 0.416940 0.076 Uiso 1 1 calc GR . . . .
C41 C 0.65184(19) 0.30472(12) 0.30439(3) 0.0293(4) Uani 1 1 d . . . . .
C42 C 0.5717(2) 0.25874(14) 0.28715(4) 0.0375(5) Uani 1 1 d . . . . .
H42 H 0.493081 0.230872 0.292709 0.045 Uiso 1 1 calc R . . . .
C43 C 0.6083(2) 0.25427(15) 0.26188(4) 0.0441(5) Uani 1 1 d . . . . .
H43 H 0.552983 0.224548 0.250488 0.053 Uiso 1 1 calc R . . . .
C44 C 0.7260(3) 0.29349(16) 0.25345(4) 0.0465(6) Uani 1 1 d . . . . .
H44 H 0.750166 0.290160 0.236419 0.056 Uiso 1 1 calc R . . . .
C45 C 0.8084(2) 0.33788(15) 0.27037(4) 0.0411(5) Uani 1 1 d . . . . .
H45 H 0.888770 0.363604 0.264799 0.049 Uiso 1 1 calc R . . . .
C46 C 0.7708(2) 0.34386(13) 0.29553(3) 0.0324(4) Uani 1 1 d . . . . .
H46 H 0.825800 0.374526 0.306768 0.039 Uiso 1 1 calc R . . . .
C47 C 0.5683(2) 0.48926(12) 0.31030(4) 0.0316(4) Uani 1 1 d . . . . .
C48 C 0.4465(2) 0.45969(14) 0.29993(4) 0.0373(5) Uani 1 1 d . . . . .
H48 H 0.391917 0.421919 0.309218 0.045 Uiso 1 1 calc R . . . .
C49 C 0.4053(3) 0.48555(15) 0.27605(4) 0.0467(6) Uani 1 1 d . . . . .
H49 H 0.322765 0.465945 0.269498 0.056 Uiso 1 1 calc R . . . .
C50 C 0.4865(3) 0.54051(16) 0.26190(4) 0.0523(6) Uani 1 1 d . . . . .
H50 H 0.459645 0.557015 0.245687 0.063 Uiso 1 1 calc R . . . .
C51 C 0.6079(3) 0.57095(16) 0.27191(4) 0.0501(6) Uani 1 1 d . . . . .
H51 H 0.662697 0.607902 0.262400 0.060 Uiso 1 1 calc R . . . .
C52 C 0.6479(2) 0.54649(14) 0.29608(4) 0.0402(5) Uani 1 1 d . . . . .
H52 H 0.728394 0.568371 0.302879 0.048 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.424(2) . ?
N1 C11 1.464(3) . ?
N1 C12 1.454(3) . ?
N2 C25 1.267(3) . ?
N2 C26 1.453(3) . ?
N3 C27 1.459(3) . ?
N3 C28 1.265(3) . ?
N4 C31 1.418(2) . ?
N4 C39 1.460(2) . ?
N4 C40 1.457(3) . ?
C1 C2 1.367(3) . ?
C1 C10 1.435(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.401(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(3) . ?
C4 C5 1.448(3) . ?
C4 C13 1.493(3) . ?
C5 C6 1.439(3) . ?
C5 C10 1.443(3) . ?
C6 C7 1.379(3) . ?
C6 C19 1.489(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.392(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.365(3) . ?
C9 C10 1.437(3) . ?
C9 C25 1.485(3) . ?
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 1.392(3) . ?
C13 C18 1.401(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.394(3) . ?
C19 C24 1.398(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.381(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.382(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.508(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28 0.9300 . ?
C28 C29 1.480(3) . ?
C29 C30 1.435(3) . ?
C29 C38 1.372(3) . ?
C30 C31 1.439(3) . ?
C30 C35 1.437(3) . ?
C31 C32 1.369(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.398(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.370(3) . ?
C34 C35 1.439(3) . ?
C34 C41 1.494(2) . ?
C35 C36 1.440(3) . ?
C36 C37 1.372(3) . ?
C36 C47 1.494(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.388(3) . ?
C38 H38 0.9300 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C42 1.395(3) . ?
C41 C46 1.394(3) . ?
C42 H42 0.9300 . ?
C42 C43 1.382(3) . ?
C43 H43 0.9300 . ?
C43 C44 1.377(3) . ?
C44 H44 0.9300 . ?
C44 C45 1.384(3) . ?
C45 H45 0.9300 . ?
C45 C46 1.380(3) . ?
C46 H46 0.9300 . ?
C47 C48 1.391(3) . ?
C47 C52 1.396(3) . ?
C48 H48 0.9300 . ?
C48 C49 1.381(3) . ?
C49 H49 0.9300 . ?
C49 C50 1.381(4) . ?
C50 H50 0.9300 . ?
C50 C51 1.384(4) . ?
C51 H51 0.9300 . ?
C51 C52 1.386(3) . ?
C52 H52 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 113.37(17) . . ?
C1 N1 C12 116.05(18) . . ?
C12 N1 C11 111.09(18) . . ?
C25 N2 C26 117.40(19) . . ?
C28 N3 C27 116.07(19) . . ?
C31 N4 C39 114.96(16) . . ?
C31 N4 C40 116.16(17) . . ?
C40 N4 C39 110.98(17) . . ?
N1 C1 C10 118.03(18) . . ?
C2 C1 N1 122.12(19) . . ?
C2 C1 C10 119.86(18) . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.5(2) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 118.88(18) . . ?
C3 C4 C13 115.75(18) . . ?
C5 C4 C13 125.08(17) . . ?
C6 C5 C4 124.20(17) . . ?
C6 C5 C10 117.97(17) . . ?
C10 C5 C4 117.81(18) . . ?
C5 C6 C19 124.91(17) . . ?
C7 C6 C5 119.22(18) . . ?
C7 C6 C19 115.84(19) . . ?
C6 C7 H7 119.0 . . ?
C6 C7 C8 122.0(2) . . ?
C8 C7 H7 119.0 . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.1(2) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C10 119.59(18) . . ?
C8 C9 C25 116.18(19) . . ?
C10 C9 C25 123.83(19) . . ?
C1 C10 C5 119.27(18) . . ?
C1 C10 C9 121.64(18) . . ?
C9 C10 C5 119.08(18) . . ?
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 120.63(17) . . ?
C14 C13 C18 118.32(18) . . ?
C18 C13 C4 120.79(17) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 120.97(19) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.16(19) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.60(19) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.33(19) . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C6 121.66(18) . . ?
C20 C19 C24 118.73(19) . . ?
C24 C19 C6 119.48(18) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.8(2) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.6(2) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.3(2) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 H24 119.8 . . ?
C23 C24 C19 120.4(2) . . ?
C23 C24 H24 119.8 . . ?
N2 C25 C9 121.2(2) . . ?
N2 C25 H25 119.4 . . ?
C9 C25 H25 119.4 . . ?
N2 C26 H26A 109.6 . . ?
N2 C26 H26B 109.6 . . ?
N2 C26 C27 110.15(18) . . ?
H26A C26 H26B 108.1 . . ?
C27 C26 H26A 109.6 . . ?
C27 C26 H26B 109.6 . . ?
N3 C27 C26 110.26(19) . . ?
N3 C27 H27A 109.6 . . ?
N3 C27 H27B 109.6 . . ?
C26 C27 H27A 109.6 . . ?
C26 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
N3 C28 H28 119.5 . . ?
N3 C28 C29 121.1(2) . . ?
C29 C28 H28 119.5 . . ?
C30 C29 C28 123.04(18) . . ?
C38 C29 C28 117.18(18) . . ?
C38 C29 C30 119.17(17) . . ?
C29 C30 C31 121.95(17) . . ?
C29 C30 C35 118.96(17) . . ?
C35 C30 C31 119.09(17) . . ?
N4 C31 C30 118.22(17) . . ?
C32 C31 N4 122.38(18) . . ?
C32 C31 C30 119.41(17) . . ?
C31 C32 H32 119.8 . . ?
C31 C32 C33 120.45(19) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 118.7 . . ?
C34 C33 C32 122.56(18) . . ?
C34 C33 H33 118.7 . . ?
C33 C34 C35 118.84(17) . . ?
C33 C34 C41 116.89(17) . . ?
C35 C34 C41 123.87(17) . . ?
C30 C35 C34 118.06(17) . . ?
C30 C35 C36 118.20(17) . . ?
C34 C35 C36 123.74(17) . . ?
C35 C36 C47 124.85(17) . . ?
C37 C36 C35 119.03(17) . . ?
C37 C36 C47 115.96(18) . . ?
C36 C37 H37 119.0 . . ?
C36 C37 C38 122.08(19) . . ?
C38 C37 H37 119.0 . . ?
C29 C38 C37 121.13(18) . . ?
C29 C38 H38 119.4 . . ?
C37 C38 H38 119.4 . . ?
N4 C39 H39A 109.5 . . ?
N4 C39 H39B 109.5 . . ?
N4 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N4 C40 H40A 109.5 . . ?
N4 C40 H40B 109.5 . . ?
N4 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C42 C41 C34 121.54(18) . . ?
C46 C41 C34 119.96(17) . . ?
C46 C41 C42 118.20(18) . . ?
C41 C42 H42 119.7 . . ?
C43 C42 C41 120.5(2) . . ?
C43 C42 H42 119.7 . . ?
C42 C43 H43 119.8 . . ?
C44 C43 C42 120.5(2) . . ?
C44 C43 H43 119.8 . . ?
C43 C44 H44 120.1 . . ?
C43 C44 C45 119.8(2) . . ?
C45 C44 H44 120.1 . . ?
C44 C45 H45 120.1 . . ?
C46 C45 C44 119.8(2) . . ?
C46 C45 H45 120.1 . . ?
C41 C46 H46 119.4 . . ?
C45 C46 C41 121.11(19) . . ?
C45 C46 H46 119.4 . . ?
C48 C47 C36 120.66(18) . . ?
C48 C47 C52 118.42(19) . . ?
C52 C47 C36 120.55(18) . . ?
C47 C48 H48 119.5 . . ?
C49 C48 C47 121.0(2) . . ?
C49 C48 H48 119.5 . . ?
C48 C49 H49 120.0 . . ?
C50 C49 C48 120.0(2) . . ?
C50 C49 H49 120.0 . . ?
C49 C50 H50 120.1 . . ?
C49 C50 C51 119.8(2) . . ?
C51 C50 H50 120.1 . . ?
C50 C51 H51 119.9 . . ?
C50 C51 C52 120.2(2) . . ?
C52 C51 H51 119.9 . . ?
C47 C52 H52 119.8 . . ?
C51 C52 C47 120.5(2) . . ?
C51 C52 H52 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 177.95(19) . . . . ?
N1 C1 C10 C5 173.06(16) . . . . ?
N1 C1 C10 C9 -7.8(3) . . . . ?
N2 C26 C27 N3 177.20(19) . . . . ?
N3 C28 C29 C30 -152.6(2) . . . . ?
N3 C28 C29 C38 36.4(3) . . . . ?
N4 C31 C32 C33 -178.53(17) . . . . ?
C1 C2 C3 C4 5.1(3) . . . . ?
C2 C1 C10 C5 -7.0(3) . . . . ?
C2 C1 C10 C9 172.13(19) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C2 C3 C4 C13 -173.06(19) . . . . ?
C3 C4 C5 C6 171.83(19) . . . . ?
C3 C4 C5 C10 -9.8(3) . . . . ?
C3 C4 C13 C14 -55.3(3) . . . . ?
C3 C4 C13 C18 118.7(2) . . . . ?
C4 C5 C6 C7 171.80(19) . . . . ?
C4 C5 C6 C19 -10.6(3) . . . . ?
C4 C5 C10 C1 12.8(3) . . . . ?
C4 C5 C10 C9 -166.43(17) . . . . ?
C4 C13 C14 C15 175.91(18) . . . . ?
C4 C13 C18 C17 -175.03(19) . . . . ?
C5 C4 C13 C14 131.0(2) . . . . ?
C5 C4 C13 C18 -55.0(3) . . . . ?
C5 C6 C7 C8 -2.0(3) . . . . ?
C5 C6 C19 C20 -50.6(3) . . . . ?
C5 C6 C19 C24 133.7(2) . . . . ?
C6 C5 C10 C1 -168.76(17) . . . . ?
C6 C5 C10 C9 12.0(3) . . . . ?
C6 C7 C8 C9 5.2(4) . . . . ?
C6 C19 C20 C21 -178.58(19) . . . . ?
C6 C19 C24 C23 177.79(19) . . . . ?
C7 C6 C19 C20 127.1(2) . . . . ?
C7 C6 C19 C24 -48.7(3) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C7 C8 C9 C25 -172.5(2) . . . . ?
C8 C9 C10 C1 171.64(19) . . . . ?
C8 C9 C10 C5 -9.2(3) . . . . ?
C8 C9 C25 N2 -42.0(3) . . . . ?
C10 C1 C2 C3 -1.9(3) . . . . ?
C10 C5 C6 C7 -6.6(3) . . . . ?
C10 C5 C6 C19 171.05(17) . . . . ?
C10 C9 C25 N2 145.3(2) . . . . ?
C11 N1 C1 C2 104.3(2) . . . . ?
C11 N1 C1 C10 -75.8(2) . . . . ?
C12 N1 C1 C2 -26.0(3) . . . . ?
C12 N1 C1 C10 153.89(19) . . . . ?
C13 C4 C5 C6 -14.7(3) . . . . ?
C13 C4 C5 C10 163.69(17) . . . . ?
C13 C14 C15 C16 -1.4(3) . . . . ?
C14 C13 C18 C17 -0.9(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C18 C13 C14 C15 1.8(3) . . . . ?
C19 C6 C7 C8 -179.9(2) . . . . ?
C19 C20 C21 C22 1.4(3) . . . . ?
C20 C19 C24 C23 1.9(3) . . . . ?
C20 C21 C22 C23 1.0(3) . . . . ?
C21 C22 C23 C24 -1.9(3) . . . . ?
C22 C23 C24 C19 0.4(3) . . . . ?
C24 C19 C20 C21 -2.8(3) . . . . ?
C25 N2 C26 C27 117.4(2) . . . . ?
C25 C9 C10 C1 -15.9(3) . . . . ?
C25 C9 C10 C5 163.30(18) . . . . ?
C26 N2 C25 C9 173.90(18) . . . . ?
C27 N3 C28 C29 -173.28(18) . . . . ?
C28 N3 C27 C26 -130.3(2) . . . . ?
C28 C29 C30 C31 19.5(3) . . . . ?
C28 C29 C30 C35 -160.33(17) . . . . ?
C28 C29 C38 C37 170.79(18) . . . . ?
C29 C30 C31 N4 9.3(3) . . . . ?
C29 C30 C31 C32 -170.53(18) . . . . ?
C29 C30 C35 C34 164.95(16) . . . . ?
C29 C30 C35 C36 -14.1(2) . . . . ?
C30 C29 C38 C37 -0.5(3) . . . . ?
C30 C31 C32 C33 1.3(3) . . . . ?
C30 C35 C36 C37 8.0(3) . . . . ?
C30 C35 C36 C47 -167.12(17) . . . . ?
C31 C30 C35 C34 -14.9(2) . . . . ?
C31 C30 C35 C36 166.11(16) . . . . ?
C31 C32 C33 C34 -6.3(3) . . . . ?
C32 C33 C34 C35 0.4(3) . . . . ?
C32 C33 C34 C41 173.42(18) . . . . ?
C33 C34 C35 C30 10.1(3) . . . . ?
C33 C34 C35 C36 -170.93(18) . . . . ?
C33 C34 C41 C42 55.2(3) . . . . ?
C33 C34 C41 C46 -118.4(2) . . . . ?
C34 C35 C36 C37 -170.98(18) . . . . ?
C34 C35 C36 C47 13.9(3) . . . . ?
C34 C41 C42 C43 -175.28(18) . . . . ?
C34 C41 C46 C45 174.16(18) . . . . ?
C35 C30 C31 N4 -170.87(16) . . . . ?
C35 C30 C31 C32 9.3(3) . . . . ?
C35 C34 C41 C42 -132.2(2) . . . . ?
C35 C34 C41 C46 54.2(3) . . . . ?
C35 C36 C37 C38 2.0(3) . . . . ?
C35 C36 C47 C48 56.9(3) . . . . ?
C35 C36 C47 C52 -130.2(2) . . . . ?
C36 C37 C38 C29 -5.9(3) . . . . ?
C36 C47 C48 C49 173.56(19) . . . . ?
C36 C47 C52 C51 -174.9(2) . . . . ?
C37 C36 C47 C48 -118.3(2) . . . . ?
C37 C36 C47 C52 54.5(3) . . . . ?
C38 C29 C30 C31 -169.70(17) . . . . ?
C38 C29 C30 C35 10.5(3) . . . . ?
C39 N4 C31 C30 71.3(2) . . . . ?
C39 N4 C31 C32 -108.9(2) . . . . ?
C40 N4 C31 C30 -156.74(19) . . . . ?
C40 N4 C31 C32 23.1(3) . . . . ?
C41 C34 C35 C30 -162.37(17) . . . . ?
C41 C34 C35 C36 16.6(3) . . . . ?
C41 C42 C43 C44 1.5(3) . . . . ?
C42 C41 C46 C45 0.4(3) . . . . ?
C42 C43 C44 C45 -0.1(3) . . . . ?
C43 C44 C45 C46 -1.1(3) . . . . ?
C44 C45 C46 C41 1.0(3) . . . . ?
C46 C41 C42 C43 -1.6(3) . . . . ?
C47 C36 C37 C38 177.48(19) . . . . ?
C47 C48 C49 C50 1.1(3) . . . . ?
C48 C47 C52 C51 -1.9(3) . . . . ?
C48 C49 C50 C51 -1.3(4) . . . . ?
C49 C50 C51 C52 -0.1(4) . . . . ?
C50 C51 C52 C47 1.7(4) . . . . ?
C52 C47 C48 C49 0.5(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 1.127
_oxdiff_exptl_absorpt_empirical_full_min 0.870
####################################################################### 
# 
# 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_jb430nofilt
_database_code_depnum_ccdc_archive 'CCDC 2069103'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 downloaded from the CCDC.
;
_audit_creation_date             2019-09-25
_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        
1-(1,1-dimethyl-5,6-diphenyl-1,2-dihydrobenzo[cd]indol-1-ium-2-yl)-2,6-dioxocyclohexan-1-ide
_chemical_formula_moiety         'C31 H27 N O2, C H Cl3'
_chemical_formula_sum            'C32 H28 Cl3 N O2'
_chemical_formula_weight         564.90
_chemical_melting_point          '423 dec.'
_chemical_oxdiff_formula         'C32 H28 O2 N1 Cl3'
_chemical_oxdiff_usercomment     'Yellow Needle Chloroform'
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'

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

_cell_length_a                   19.4622(12)
_cell_length_b                   9.9340(8)
_cell_length_c                   29.6756(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.325(5)
_cell_angle_gamma                90
_cell_volume                     5727.7(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1591
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      21.1340
_cell_measurement_theta_min      2.6240
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.848
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.881
_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    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -14 4 0.2295
-1 -1 -42 0.0493
2 1 41 0.0082
27 0 -6 0.0198
-27 0 6 0.0499
-1 14 -4 0.2529

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.486
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
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
0.9924 -14.0245 4.0135 -0.5753 -0.7356 -0.3747
-1.0111 -1.0469 -41.9542 0.7968 -0.6179 0.0582
2.0106 1.0457 40.9552 -0.7906 0.5959 -0.0224
26.9919 -0.0091 -5.9964 -0.2425 -0.3095 0.9066
-26.9919 0.0091 5.9964 0.2425 0.3095 -0.9066
-0.9924 14.0245 -4.0135 0.5753 0.7356 0.3747

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1084
_diffrn_reflns_av_unetI/netI     0.1426
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            20831
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.096
_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 1.000
_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    -91.00 -37.00   1.00   60.00    --  -19.89 154.00 -15.00   54
  2  ω    -71.00 -14.00   1.00   60.00    --  -19.89 120.00-173.00   57
  3  ω     35.00  92.00   1.00   60.00    --   20.05 178.00 -90.00   57
  4  ω      1.00  87.00   1.00   60.00    --   20.05  37.00  30.00   86
  5  φ    265.00 345.00   1.00   60.00  24.36  20.05 -20.00    --    80
  6  ω     46.00  92.00   1.00   60.00    --   20.05 178.00 120.00   46
;
_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      -0.0133114000
_diffrn_orient_matrix_UB_12      0.0344904000
_diffrn_orient_matrix_UB_13      -0.0195313000
_diffrn_orient_matrix_UB_21      -0.0084386000
_diffrn_orient_matrix_UB_22      0.0557262000
_diffrn_orient_matrix_UB_23      0.0135409000
_diffrn_orient_matrix_UB_31      0.0329571000
_diffrn_orient_matrix_UB_32      0.0282246000
_diffrn_orient_matrix_UB_33      -0.0028846000
_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                2821
_reflns_number_total             5880
_reflns_odcompleteness_completeness 99.88
_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.
 
disordered chloroform molecule
;
_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         0.398
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5880
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1795
_refine_ls_R_factor_gt           0.0805
_refine_ls_restrained_S_all      1.018
_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)+(0.0434P)²+2.5905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1734
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H32A)=Sof(Cl3B)=Sof(Cl1B)=Sof(Cl2B)=1-FVAR(1)
 Sof(H32)=Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C25(H25), C32(H32), C32(H32A)
3.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C30(H30A,H30B), C28(H28A,H28B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C20(H20), C8(H8), C2(H2), C3(H3), C18(H18), C17(H17), C24(H24),
 C14(H14), C21(H21), C16(H16), C15(H15), C23(H23), C22(H22)
3.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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
O2 O 0.46247(12) 0.6494(2) 0.80595(7) 0.0331(6) Uani 1 1 d . . . . .
O1 O 0.27762(12) 0.3532(3) 0.82207(8) 0.0372(7) Uani 1 1 d . . . . .
N1 N 0.40232(14) 0.3886(3) 0.73808(9) 0.0282(7) Uani 1 1 d . . . . .
C31 C 0.41553(18) 0.6027(4) 0.82870(11) 0.0290(9) Uani 1 1 d . . . . .
C19 C 0.36333(16) 0.8911(4) 0.61691(11) 0.0248(8) Uani 1 1 d . . . . .
C6 C 0.37057(17) 0.7962(4) 0.65573(11) 0.0255(9) Uani 1 1 d . . . . .
C1 C 0.41663(17) 0.4489(4) 0.69377(11) 0.0264(9) Uani 1 1 d . . . . .
C5 C 0.40140(16) 0.6639(4) 0.65313(11) 0.0239(8) Uani 1 1 d . . . . .
C26 C 0.36348(17) 0.5149(4) 0.81034(11) 0.0262(9) Uani 1 1 d . . . . .
C27 C 0.31849(18) 0.4419(4) 0.83763(12) 0.0298(9) Uani 1 1 d . . . . .
C10 C 0.39408(17) 0.5817(4) 0.69138(11) 0.0263(9) Uani 1 1 d . . . . .
C13 C 0.45480(17) 0.6710(4) 0.57471(11) 0.0267(9) Uani 1 1 d . . . . .
C7 C 0.34206(17) 0.8333(4) 0.69559(11) 0.0292(9) Uani 1 1 d . . . . .
H7 H 0.324919 0.920349 0.697626 0.035 Uiso 1 1 calc R . . . .
C9 C 0.36175(17) 0.6196(4) 0.73036(11) 0.0250(9) Uani 1 1 d . . . . .
C20 C 0.33323(17) 0.8498(4) 0.57547(11) 0.0322(9) Uani 1 1 d . . . . .
H20 H 0.317859 0.761596 0.571883 0.039 Uiso 1 1 calc R . . . .
C25 C 0.35372(18) 0.4992(4) 0.76066(11) 0.0270(9) Uani 1 1 d . . . . .
H25 H 0.306335 0.467651 0.754777 0.032 Uiso 1 1 calc R . . . .
C8 C 0.33723(17) 0.7477(4) 0.73351(11) 0.0296(9) Uani 1 1 d . . . . .
H8 H 0.318004 0.777883 0.759638 0.035 Uiso 1 1 calc R . . . .
C2 C 0.44843(18) 0.3880(4) 0.65966(12) 0.0338(10) Uani 1 1 d . . . . .
H2 H 0.463061 0.298942 0.661355 0.041 Uiso 1 1 calc R . . . .
C4 C 0.43685(17) 0.6018(4) 0.61697(11) 0.0285(9) Uani 1 1 d . . . . .
C3 C 0.45771(18) 0.4691(4) 0.62155(12) 0.0350(10) Uani 1 1 d . . . . .
H3 H 0.479512 0.430503 0.597655 0.042 Uiso 1 1 calc R . . . .
C18 C 0.49538(17) 0.7867(4) 0.57520(12) 0.0309(9) Uani 1 1 d . . . . .
H18 H 0.509986 0.825355 0.602643 0.037 Uiso 1 1 calc R . . . .
C17 C 0.51418(18) 0.8446(4) 0.53538(12) 0.0373(10) Uani 1 1 d . . . . .
H17 H 0.541669 0.921210 0.536119 0.045 Uiso 1 1 calc R . . . .
C24 C 0.38383(19) 1.0254(4) 0.62134(12) 0.0346(10) Uani 1 1 d . . . . .
H24 H 0.403634 1.055514 0.648777 0.042 Uiso 1 1 calc R . . . .
C14 C 0.43425(18) 0.6145(4) 0.53301(12) 0.0350(10) Uani 1 1 d . . . . .
H14 H 0.408086 0.536095 0.532092 0.042 Uiso 1 1 calc R . . . .
C29 C 0.34731(19) 0.6115(4) 0.89918(12) 0.0384(10) Uani 1 1 d . . . . .
H29A H 0.352790 0.621854 0.931694 0.046 Uiso 1 1 calc R . . . .
H29B H 0.313787 0.677147 0.887695 0.046 Uiso 1 1 calc R . . . .
C30 C 0.41591(19) 0.6366(4) 0.87847(11) 0.0364(10) Uani 1 1 d . . . . .
H30A H 0.428139 0.730709 0.882526 0.044 Uiso 1 1 calc R . . . .
H30B H 0.451116 0.583315 0.894586 0.044 Uiso 1 1 calc R . . . .
C28 C 0.32177(19) 0.4709(4) 0.88775(11) 0.0363(10) Uani 1 1 d . . . . .
H28A H 0.352089 0.405949 0.903116 0.044 Uiso 1 1 calc R . . . .
H28B H 0.276244 0.459527 0.898887 0.044 Uiso 1 1 calc R . . . .
C21 C 0.32589(18) 0.9391(5) 0.53937(12) 0.0398(11) Uani 1 1 d . . . . .
H21 H 0.306743 0.909747 0.511651 0.048 Uiso 1 1 calc R . . . .
C16 C 0.4919(2) 0.7881(4) 0.49419(12) 0.0411(11) Uani 1 1 d . . . . .
H16 H 0.503909 0.827952 0.467409 0.049 Uiso 1 1 calc R . . . .
C15 C 0.4521(2) 0.6731(4) 0.49292(12) 0.0402(11) Uani 1 1 d . . . . .
H15 H 0.437406 0.635213 0.465378 0.048 Uiso 1 1 calc R . . . .
C23 C 0.3752(2) 1.1144(4) 0.58562(13) 0.0441(11) Uani 1 1 d . . . . .
H23 H 0.388503 1.203753 0.589400 0.053 Uiso 1 1 calc R . . . .
C11 C 0.46857(19) 0.3658(4) 0.76562(12) 0.0425(11) Uani 1 1 d . . . . .
H11A H 0.496750 0.303565 0.750189 0.064 Uiso 1 1 calc GR . . . .
H11B H 0.458736 0.329453 0.794527 0.064 Uiso 1 1 calc GR . . . .
H11C H 0.492530 0.449742 0.769742 0.064 Uiso 1 1 calc GR . . . .
C22 C 0.3471(2) 1.0715(5) 0.54465(13) 0.0448(11) Uani 1 1 d . . . . .
H22 H 0.342239 1.131127 0.520518 0.054 Uiso 1 1 calc R . . . .
C12 C 0.3649(2) 0.2575(4) 0.73272(13) 0.0439(11) Uani 1 1 d . . . . .
H12A H 0.325016 0.269092 0.712508 0.066 Uiso 1 1 calc GR . . . .
H12B H 0.350906 0.227928 0.761591 0.066 Uiso 1 1 calc GR . . . .
H12C H 0.394759 0.191442 0.720631 0.066 Uiso 1 1 calc GR . . . .
C32 C 0.2945(2) 0.0910(5) 0.88053(17) 0.0732(16) Uani 1 1 d . . . . .
H32 H 0.283153 0.179318 0.867360 0.088 Uiso 0.564(5) 1 calc R . P A 1
H32A H 0.277945 0.177379 0.868154 0.088 Uiso 0.436(5) 1 calc R . P A 2
Cl1A Cl 0.36877(15) 0.1008(3) 0.90646(17) 0.0993(18) Uani 0.564(5) 1 d . . P A
1
Cl2A Cl 0.2877(3) -0.0327(4) 0.83610(12) 0.1170(18) Uani 0.564(5) 1 d . . P A 1
Cl3A Cl 0.2298(2) 0.0481(4) 0.91819(16) 0.1187(19) Uani 0.564(5) 1 d . . P A 1
Cl3B Cl 0.3164(5) 0.1119(6) 0.9418(2) 0.208(4) Uani 0.436(5) 1 d . . P A 2
Cl1B Cl 0.3801(3) 0.0598(7) 0.8617(3) 0.187(4) Uani 0.436(5) 1 d . . P A 2
Cl2B Cl 0.2419(4) -0.0131(6) 0.8695(3) 0.214(7) Uani 0.436(5) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C31 1.256(4) . ?
O1 C27 1.257(4) . ?
N1 C1 1.486(4) . ?
N1 C25 1.620(4) . ?
N1 C11 1.503(4) . ?
N1 C12 1.496(4) . ?
C31 C26 1.422(5) . ?
C31 C30 1.515(5) . ?
C19 C6 1.489(5) . ?
C19 C20 1.393(4) . ?
C19 C24 1.397(5) . ?
C6 C5 1.449(5) . ?
C6 C7 1.385(4) . ?
C1 C10 1.391(5) . ?
C1 C2 1.359(5) . ?
C5 C10 1.412(5) . ?
C5 C4 1.447(5) . ?
C26 C27 1.425(5) . ?
C26 C25 1.484(4) . ?
C27 C28 1.513(5) . ?
C10 C9 1.400(4) . ?
C13 C4 1.489(5) . ?
C13 C18 1.393(5) . ?
C13 C14 1.396(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.418(5) . ?
C9 C25 1.510(5) . ?
C9 C8 1.365(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.392(5) . ?
C25 H25 0.9800 . ?
C8 H8 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.409(5) . ?
C4 C3 1.384(5) . ?
C3 H3 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.383(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.391(5) . ?
C24 H24 0.9300 . ?
C24 C23 1.383(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.387(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.522(5) . ?
C29 C28 1.515(5) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C21 H21 0.9300 . ?
C21 C22 1.385(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.379(5) . ?
C15 H15 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.372(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C22 H22 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C32 H32 0.9800 . ?
C32 H32A 0.9800 . ?
C32 Cl1A 1.601(5) . ?
C32 Cl2A 1.802(6) . ?
C32 Cl3A 1.782(6) . ?
C32 Cl3B 1.854(8) . ?
C32 Cl1B 1.816(7) . ?
C32 Cl2B 1.478(6) . ?

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 C25 103.7(3) . . ?
C1 N1 C11 110.1(3) . . ?
C1 N1 C12 111.8(3) . . ?
C11 N1 C25 112.3(3) . . ?
C12 N1 C25 110.0(3) . . ?
C12 N1 C11 108.9(3) . . ?
O2 C31 C26 123.0(3) . . ?
O2 C31 C30 118.6(3) . . ?
C26 C31 C30 118.3(3) . . ?
C20 C19 C6 120.9(3) . . ?
C20 C19 C24 117.9(3) . . ?
C24 C19 C6 121.2(3) . . ?
C5 C6 C19 123.6(3) . . ?
C7 C6 C19 117.9(3) . . ?
C7 C6 C5 118.3(3) . . ?
C10 C1 N1 110.7(3) . . ?
C2 C1 N1 126.7(3) . . ?
C2 C1 C10 122.7(3) . . ?
C10 C5 C6 114.9(3) . . ?
C10 C5 C4 115.1(3) . . ?
C4 C5 C6 130.0(3) . . ?
C31 C26 C27 122.8(3) . . ?
C31 C26 C25 119.5(3) . . ?
C27 C26 C25 117.6(3) . . ?
O1 C27 C26 123.0(3) . . ?
O1 C27 C28 119.0(3) . . ?
C26 C27 C28 118.0(3) . . ?
C1 C10 C5 122.9(3) . . ?
C1 C10 C9 111.6(3) . . ?
C9 C10 C5 125.4(3) . . ?
C18 C13 C4 122.2(3) . . ?
C18 C13 C14 118.3(3) . . ?
C14 C13 C4 119.4(3) . . ?
C6 C7 H7 117.7 . . ?
C6 C7 C8 124.5(3) . . ?
C8 C7 H7 117.7 . . ?
C10 C9 C25 110.3(3) . . ?
C8 C9 C10 118.9(3) . . ?
C8 C9 C25 130.5(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.7(4) . . ?
C21 C20 H20 119.6 . . ?
N1 C25 H25 106.0 . . ?
C26 C25 N1 116.0(3) . . ?
C26 C25 C9 119.8(3) . . ?
C26 C25 H25 106.0 . . ?
C9 C25 N1 102.0(3) . . ?
C9 C25 H25 106.0 . . ?
C7 C8 H8 121.1 . . ?
C9 C8 C7 117.8(3) . . ?
C9 C8 H8 121.1 . . ?
C1 C2 H2 122.3 . . ?
C1 C2 C3 115.4(4) . . ?
C3 C2 H2 122.3 . . ?
C5 C4 C13 124.9(3) . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 C13 116.2(3) . . ?
C2 C3 H3 117.5 . . ?
C4 C3 C2 125.0(3) . . ?
C4 C3 H3 117.5 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.8(3) . . ?
C17 C18 H18 119.6 . . ?
C18 C17 H17 120.0 . . ?
C18 C17 C16 119.9(4) . . ?
C16 C17 H17 120.0 . . ?
C19 C24 H24 119.4 . . ?
C23 C24 C19 121.1(4) . . ?
C23 C24 H24 119.4 . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.2(4) . . ?
C15 C14 H14 119.4 . . ?
H29A C29 H29B 108.1 . . ?
C30 C29 H29A 109.6 . . ?
C30 C29 H29B 109.6 . . ?
C28 C29 H29A 109.6 . . ?
C28 C29 H29B 109.6 . . ?
C28 C29 C30 110.2(3) . . ?
C31 C30 C29 113.7(3) . . ?
C31 C30 H30A 108.8 . . ?
C31 C30 H30B 108.8 . . ?
C29 C30 H30A 108.8 . . ?
C29 C30 H30B 108.8 . . ?
H30A C30 H30B 107.7 . . ?
C27 C28 C29 113.0(3) . . ?
C27 C28 H28A 109.0 . . ?
C27 C28 H28B 109.0 . . ?
C29 C28 H28A 109.0 . . ?
C29 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.1(4) . . ?
C22 C21 H21 119.9 . . ?
C17 C16 H16 119.9 . . ?
C15 C16 C17 120.3(4) . . ?
C15 C16 H16 119.9 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.5(4) . . ?
C16 C15 H15 120.2 . . ?
C24 C23 H23 119.8 . . ?
C22 C23 C24 120.4(4) . . ?
C22 C23 H23 119.8 . . ?
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 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.7(4) . . ?
C23 C22 H22 120.1 . . ?
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 . . ?
Cl1A C32 H32 108.3 . . ?
Cl1A C32 Cl2A 114.8(4) . . ?
Cl1A C32 Cl3A 111.3(4) . . ?
Cl2A C32 H32 108.3 . . ?
Cl3A C32 H32 108.3 . . ?
Cl3A C32 Cl2A 105.7(3) . . ?
Cl3B C32 H32A 108.8 . . ?
Cl1B C32 H32A 108.8 . . ?
Cl1B C32 Cl3B 99.1(5) . . ?
Cl2B C32 H32A 108.8 . . ?
Cl2B C32 Cl3B 114.3(5) . . ?
Cl2B C32 Cl1B 116.7(6) . . ?

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
O2 C31 C26 C27 167.6(4) . . . . ?
O2 C31 C26 C25 -13.7(6) . . . . ?
O2 C31 C30 C29 162.7(3) . . . . ?
O1 C27 C28 C29 -155.4(3) . . . . ?
N1 C1 C10 C5 179.7(3) . . . . ?
N1 C1 C10 C9 -2.5(4) . . . . ?
N1 C1 C2 C3 -178.0(3) . . . . ?
C31 C26 C27 O1 -171.9(3) . . . . ?
C31 C26 C27 C28 6.5(5) . . . . ?
C31 C26 C25 N1 85.5(4) . . . . ?
C31 C26 C25 C9 -37.5(5) . . . . ?
C19 C6 C5 C10 -170.8(3) . . . . ?
C19 C6 C5 C4 7.3(6) . . . . ?
C19 C6 C7 C8 171.9(3) . . . . ?
C19 C20 C21 C22 -1.6(5) . . . . ?
C19 C24 C23 C22 -1.0(6) . . . . ?
C6 C19 C20 C21 179.3(3) . . . . ?
C6 C19 C24 C23 -178.1(3) . . . . ?
C6 C5 C10 C1 175.9(3) . . . . ?
C6 C5 C10 C9 -1.5(5) . . . . ?
C6 C5 C4 C13 6.1(6) . . . . ?
C6 C5 C4 C3 -175.5(3) . . . . ?
C6 C7 C8 C9 -0.7(5) . . . . ?
C1 N1 C25 C26 -144.8(3) . . . . ?
C1 N1 C25 C9 -12.8(3) . . . . ?
C1 C10 C9 C25 -6.8(4) . . . . ?
C1 C10 C9 C8 179.4(3) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C5 C6 C7 C8 -3.9(5) . . . . ?
C5 C10 C9 C25 170.9(3) . . . . ?
C5 C10 C9 C8 -2.9(5) . . . . ?
C5 C4 C3 C2 -1.4(6) . . . . ?
C26 C31 C30 C29 -19.8(5) . . . . ?
C26 C27 C28 C29 26.1(5) . . . . ?
C27 C26 C25 N1 -95.7(4) . . . . ?
C27 C26 C25 C9 141.2(3) . . . . ?
C10 C1 C2 C3 0.5(5) . . . . ?
C10 C5 C4 C13 -175.8(3) . . . . ?
C10 C5 C4 C3 2.6(5) . . . . ?
C10 C9 C25 N1 12.1(3) . . . . ?
C10 C9 C25 C26 141.8(3) . . . . ?
C10 C9 C8 C7 3.9(5) . . . . ?
C13 C4 C3 C2 177.1(3) . . . . ?
C13 C18 C17 C16 0.7(6) . . . . ?
C13 C14 C15 C16 1.1(6) . . . . ?
C7 C6 C5 C10 4.7(4) . . . . ?
C7 C6 C5 C4 -177.2(3) . . . . ?
C20 C19 C6 C5 51.6(5) . . . . ?
C20 C19 C6 C7 -123.9(4) . . . . ?
C20 C19 C24 C23 -0.6(5) . . . . ?
C20 C21 C22 C23 -0.1(6) . . . . ?
C25 N1 C1 C10 9.9(3) . . . . ?
C25 N1 C1 C2 -171.4(3) . . . . ?
C25 C26 C27 O1 9.4(5) . . . . ?
C25 C26 C27 C28 -172.2(3) . . . . ?
C25 C9 C8 C7 -168.4(3) . . . . ?
C8 C9 C25 N1 -175.0(3) . . . . ?
C8 C9 C25 C26 -45.4(5) . . . . ?
C2 C1 C10 C5 0.9(5) . . . . ?
C2 C1 C10 C9 178.7(3) . . . . ?
C4 C5 C10 C1 -2.5(5) . . . . ?
C4 C5 C10 C9 -180.0(3) . . . . ?
C4 C13 C18 C17 176.6(3) . . . . ?
C4 C13 C14 C15 -177.6(3) . . . . ?
C18 C13 C4 C5 57.8(5) . . . . ?
C18 C13 C4 C3 -120.6(4) . . . . ?
C18 C13 C14 C15 -1.5(5) . . . . ?
C18 C17 C16 C15 -1.1(6) . . . . ?
C17 C16 C15 C14 0.2(6) . . . . ?
C24 C19 C6 C5 -131.1(4) . . . . ?
C24 C19 C6 C7 53.4(4) . . . . ?
C24 C19 C20 C21 1.9(5) . . . . ?
C24 C23 C22 C21 1.4(6) . . . . ?
C14 C13 C4 C5 -126.3(4) . . . . ?
C14 C13 C4 C3 55.3(4) . . . . ?
C14 C13 C18 C17 0.6(5) . . . . ?
C30 C31 C26 C27 -9.7(5) . . . . ?
C30 C31 C26 C25 168.9(3) . . . . ?
C30 C29 C28 C27 -53.6(4) . . . . ?
C28 C29 C30 C31 50.6(4) . . . . ?
C11 N1 C1 C10 -110.5(3) . . . . ?
C11 N1 C1 C2 68.2(4) . . . . ?
C11 N1 C25 C26 -26.0(4) . . . . ?
C11 N1 C25 C9 106.0(3) . . . . ?
C12 N1 C1 C10 128.3(3) . . . . ?
C12 N1 C1 C2 -53.0(5) . . . . ?
C12 N1 C25 C26 95.5(3) . . . . ?
C12 N1 C25 C9 -132.6(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 1.235
_oxdiff_exptl_absorpt_empirical_full_min 0.831
####################################################################### 
# 
# 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_staceychoabs150k
_database_code_depnum_ccdc_archive 'CCDC 2069101'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 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        
;
1-Dimethylamino-4,5-diphenylnaphthalene-8-carbaldehyde
;
_chemical_formula_moiety         'C25 H21 N O'
_chemical_formula_sum            'C25 H21 N O'
_chemical_formula_weight         351.43
_chemical_melting_point          450-452
_chemical_oxdiff_formula         'C25 H21 N1 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.6676(5)
_cell_length_b                   9.9541(3)
_cell_length_c                   15.1783(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.164(4)
_cell_angle_gamma                90
_cell_volume                     1818.53(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6776
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.9130
_cell_measurement_theta_min      3.8130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.842
_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            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
15 1 -16 0.0318
-15 -1 16 0.0669
7 8 12 0.1940
-7 -8 -11 0.1578
-6 -3 -17 0.1190
6 2 17 0.1752
7 -10 10 0.1945
3 -14 -4 0.1572
-3 14 4 0.1748

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.322
_exptl_crystal_size_min          0.099
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
15.0000 1.0000 -16.0000 -0.9217 -0.2764 0.2142
-15.0000 -1.0000 16.0000 0.9217 0.2764 -0.2142
7.0000 8.0000 12.0000 -0.2032 -0.0838 -0.9738
-7.0000 -8.0000 -11.0000 0.2264 0.0665 0.9341
-6.0000 -3.0000 -17.0000 -0.0979 0.3845 0.9477
6.0000 2.0000 17.0000 0.1279 -0.4353 -0.9079
7.0000 -10.0000 10.0000 0.2906 -0.9642 -0.1768
3.0000 -14.0000 -4.0000 0.2233 -0.7633 0.6406
-3.0000 14.0000 4.0000 -0.2233 0.7633 -0.6406

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19390
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.385
_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 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  84.00   1.00   22.50    --   16.24  57.00 150.00   84
  2  ω      0.00  84.00   1.00   22.50    --   16.24  57.00-120.00   84
  3  ω      0.00  84.00   1.00   22.50    --   16.24  57.00 -60.00   84
  4  ω      0.00  84.00   1.00   22.50    --   16.24  57.00  90.00   84
  5  ω    -51.00  33.00   1.00   22.50    --   16.24 -57.00 -60.00   84
  6  ω    -51.00 -26.00   1.00   22.50    --   16.24 -57.00  30.00   25
  7  ω    -51.00  33.00   1.00   22.50    --   16.24 -57.00 150.00   84
;
_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      -0.0346187000
_diffrn_orient_matrix_UB_12      -0.0300148000
_diffrn_orient_matrix_UB_13      0.0232737000
_diffrn_orient_matrix_UB_21      -0.0403283000
_diffrn_orient_matrix_UB_22      0.0508370000
_diffrn_orient_matrix_UB_23      -0.0173527000
_diffrn_orient_matrix_UB_31      -0.0254430000
_diffrn_orient_matrix_UB_32      -0.0398594000
_diffrn_orient_matrix_UB_33      -0.0397341000
_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                3300
_reflns_number_total             3708
_reflns_odcompleteness_completeness 99.72
_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.
 
some evidence of a small degree of disorder in which the molecule
is turned over about the short axis of the naphthalene
;
_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         0.669
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0721
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0896P)²+1.9864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1891
_refine_ls_wR_factor_ref         0.1953
_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)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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 0.65519(15) 0.5473(2) 0.12804(13) 0.0414(5) Uani 1 1 d . . . . .
N1 N 0.68063(16) 0.6357(2) 0.32211(14) 0.0303(5) Uani 1 1 d . . . . .
C1 C 0.57582(19) 0.6414(2) 0.34132(17) 0.0292(5) Uani 1 1 d . . . . .
C2 C 0.5649(2) 0.6566(3) 0.42723(19) 0.0358(6) Uani 1 1 d . . . . .
H2 H 0.627326 0.669630 0.478516 0.043 Uiso 1 1 calc R . . . .
C3 C 0.4578(2) 0.6524(3) 0.43803(17) 0.0338(6) Uani 1 1 d . . . . .
H3 H 0.451547 0.663340 0.497055 0.041 Uiso 1 1 calc R . . . .
C4 C 0.36208(19) 0.6326(2) 0.36422(16) 0.0265(5) Uani 1 1 d . . . . .
C5 C 0.37069(18) 0.6238(2) 0.27173(16) 0.0237(5) Uani 1 1 d . . . . .
C6 C 0.27934(18) 0.6110(2) 0.18704(16) 0.0244(5) Uani 1 1 d . . . . .
C7 C 0.3022(2) 0.5886(2) 0.10442(17) 0.0298(5) Uani 1 1 d . . . . .
H7 H 0.242899 0.573534 0.050989 0.036 Uiso 1 1 calc R . . . .
C8 C 0.4100(2) 0.5876(2) 0.09737(17) 0.0306(5) Uani 1 1 d . . . . .
H8 H 0.421323 0.570304 0.040768 0.037 Uiso 1 1 calc R . . . .
C9 C 0.4978(2) 0.6121(2) 0.17436(17) 0.0287(5) Uani 1 1 d . . . . .
C10 C 0.48061(19) 0.6274(2) 0.26257(17) 0.0263(5) Uani 1 1 d . . . . .
C11 C 0.7359(2) 0.5056(3) 0.3436(2) 0.0403(6) Uani 1 1 d . . . . .
H11A H 0.760608 0.492287 0.409474 0.060 Uiso 1 1 calc GR . . . .
H11B H 0.798597 0.503433 0.320836 0.060 Uiso 1 1 calc GR . . . .
H11C H 0.684736 0.435665 0.314444 0.060 Uiso 1 1 calc GR . . . .
C12 C 0.7562(2) 0.7468(3) 0.3619(3) 0.0517(8) Uani 1 1 d . . . . .
H12A H 0.717945 0.830636 0.344404 0.078 Uiso 1 1 calc GR . . . .
H12B H 0.818852 0.743515 0.339033 0.078 Uiso 1 1 calc GR . . . .
H12C H 0.781497 0.739128 0.428217 0.078 Uiso 1 1 calc GR . . . .
C13 C 0.25606(19) 0.6182(2) 0.38744(15) 0.0262(5) Uani 1 1 d . . . . .
C14 C 0.2204(2) 0.7225(2) 0.43318(17) 0.0326(6) Uani 1 1 d . . . . .
H14 H 0.264565 0.798524 0.451242 0.039 Uiso 1 1 calc R . . . .
C15 C 0.1205(2) 0.7142(3) 0.45191(18) 0.0367(6) Uani 1 1 d . . . . .
H15 H 0.096914 0.785634 0.480605 0.044 Uiso 1 1 calc R . . . .
C16 C 0.0551(2) 0.5994(3) 0.42793(18) 0.0361(6) Uani 1 1 d . . . . .
H16 H -0.012503 0.594110 0.439793 0.043 Uiso 1 1 calc R . . . .
C17 C 0.0916(2) 0.4931(3) 0.38625(18) 0.0332(6) Uani 1 1 d . . . . .
H17 H 0.049151 0.415230 0.371568 0.040 Uiso 1 1 calc R . . . .
C18 C 0.19103(19) 0.5016(2) 0.36618(16) 0.0280(5) Uani 1 1 d . . . . .
H18 H 0.214707 0.429290 0.338376 0.034 Uiso 1 1 calc R . . . .
C19 C 0.15927(18) 0.6256(2) 0.17933(15) 0.0245(5) Uani 1 1 d . . . . .
C20 C 0.11902(19) 0.7407(2) 0.21047(17) 0.0288(5) Uani 1 1 d . . . . .
H20 H 0.167807 0.809470 0.238120 0.035 Uiso 1 1 calc R . . . .
C21 C 0.0068(2) 0.7534(3) 0.20053(19) 0.0357(6) Uani 1 1 d . . . . .
H21 H -0.018826 0.829958 0.222540 0.043 Uiso 1 1 calc R . . . .
C22 C -0.0675(2) 0.6528(3) 0.15796(19) 0.0387(6) Uani 1 1 d . . . . .
H22 H -0.142560 0.661311 0.151703 0.046 Uiso 1 1 calc R . . . .
C23 C -0.0287(2) 0.5400(3) 0.12500(18) 0.0374(6) Uani 1 1 d . . . . .
H23 H -0.078327 0.472919 0.095543 0.045 Uiso 1 1 calc R . . . .
C24 C 0.0834(2) 0.5255(2) 0.13537(17) 0.0305(5) Uani 1 1 d . . . . .
H24 H 0.108324 0.448855 0.112974 0.037 Uiso 1 1 calc R . . . .
C25 C 0.6109(2) 0.6320(3) 0.16227(17) 0.0331(6) Uani 1 1 d . . . . .
H25 H 0.648120 0.712524 0.181839 0.040 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C25 1.216(3) . ?
N1 C1 1.446(3) . ?
N1 C11 1.459(3) . ?
N1 C12 1.464(3) . ?
C1 C2 1.362(4) . ?
C1 C10 1.416(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.417(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 C5 1.444(3) . ?
C4 C13 1.498(3) . ?
C5 C6 1.442(3) . ?
C5 C10 1.442(3) . ?
C6 C7 1.390(3) . ?
C6 C19 1.496(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.402(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.361(3) . ?
C9 C10 1.430(3) . ?
C9 C25 1.513(3) . ?
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 1.400(3) . ?
C13 C18 1.401(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.392(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.396(3) . ?
C19 C24 1.400(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.388(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.388(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.380(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.386(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 113.33(19) . . ?
C1 N1 C12 114.3(2) . . ?
C11 N1 C12 111.8(2) . . ?
C2 C1 N1 124.8(2) . . ?
C2 C1 C10 120.3(2) . . ?
C10 C1 N1 114.8(2) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 118.7 . . ?
C4 C3 C2 122.6(2) . . ?
C4 C3 H3 118.7 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 C13 116.5(2) . . ?
C5 C4 C13 124.6(2) . . ?
C6 C5 C4 126.1(2) . . ?
C10 C5 C4 117.4(2) . . ?
C10 C5 C6 116.5(2) . . ?
C5 C6 C19 125.1(2) . . ?
C7 C6 C5 118.9(2) . . ?
C7 C6 C19 116.0(2) . . ?
C6 C7 H7 118.3 . . ?
C6 C7 C8 123.5(2) . . ?
C8 C7 H7 118.3 . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.2(2) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 120.0(2) . . ?
C8 C9 C25 118.1(2) . . ?
C10 C9 C25 121.7(2) . . ?
C1 C10 C5 121.0(2) . . ?
C1 C10 C9 117.5(2) . . ?
C9 C10 C5 121.4(2) . . ?
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 119.8(2) . . ?
C14 C13 C18 118.1(2) . . ?
C18 C13 C4 122.1(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.4(2) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.6(2) . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C6 121.5(2) . . ?
C20 C19 C24 118.4(2) . . ?
C24 C19 C6 119.9(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.5(2) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.3(2) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.7(2) . . ?
C24 C23 H23 119.7 . . ?
C19 C24 H24 119.8 . . ?
C23 C24 C19 120.5(2) . . ?
C23 C24 H24 119.8 . . ?
O1 C25 C9 122.7(2) . . ?
O1 C25 H25 118.6 . . ?
C9 C25 H25 118.6 . . ?

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 -176.1(2) . . . . ?
N1 C1 C10 C5 176.64(19) . . . . ?
N1 C1 C10 C9 -1.1(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C1 C10 C5 -2.4(3) . . . . ?
C2 C1 C10 C9 179.9(2) . . . . ?
C2 C3 C4 C5 -3.7(4) . . . . ?
C2 C3 C4 C13 174.6(2) . . . . ?
C3 C4 C5 C6 -176.3(2) . . . . ?
C3 C4 C5 C10 4.0(3) . . . . ?
C3 C4 C13 C14 59.7(3) . . . . ?
C3 C4 C13 C18 -119.3(2) . . . . ?
C4 C5 C6 C7 -172.9(2) . . . . ?
C4 C5 C6 C19 9.8(3) . . . . ?
C4 C5 C10 C1 -1.1(3) . . . . ?
C4 C5 C10 C9 176.62(19) . . . . ?
C4 C13 C14 C15 177.2(2) . . . . ?
C4 C13 C18 C17 -178.1(2) . . . . ?
C5 C4 C13 C14 -122.0(2) . . . . ?
C5 C4 C13 C18 59.0(3) . . . . ?
C5 C6 C7 C8 -4.9(3) . . . . ?
C5 C6 C19 C20 55.1(3) . . . . ?
C5 C6 C19 C24 -128.5(2) . . . . ?
C6 C5 C10 C1 179.21(19) . . . . ?
C6 C5 C10 C9 -3.1(3) . . . . ?
C6 C7 C8 C9 -1.3(4) . . . . ?
C6 C19 C20 C21 178.4(2) . . . . ?
C6 C19 C24 C23 -177.8(2) . . . . ?
C7 C6 C19 C20 -122.3(2) . . . . ?
C7 C6 C19 C24 54.1(3) . . . . ?
C7 C8 C9 C10 5.2(3) . . . . ?
C7 C8 C9 C25 -170.5(2) . . . . ?
C8 C9 C10 C1 174.8(2) . . . . ?
C8 C9 C10 C5 -3.0(3) . . . . ?
C8 C9 C25 O1 -58.9(3) . . . . ?
C10 C1 C2 C3 2.8(4) . . . . ?
C10 C5 C6 C7 6.8(3) . . . . ?
C10 C5 C6 C19 -170.51(19) . . . . ?
C10 C9 C25 O1 125.4(3) . . . . ?
C11 N1 C1 C2 78.0(3) . . . . ?
C11 N1 C1 C10 -100.9(2) . . . . ?
C12 N1 C1 C2 -51.6(3) . . . . ?
C12 N1 C1 C10 129.4(3) . . . . ?
C13 C4 C5 C6 5.4(3) . . . . ?
C13 C4 C5 C10 -174.26(19) . . . . ?
C13 C14 C15 C16 2.0(4) . . . . ?
C14 C13 C18 C17 2.9(3) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
C15 C16 C17 C18 -1.7(4) . . . . ?
C16 C17 C18 C13 -0.2(4) . . . . ?
C18 C13 C14 C15 -3.8(4) . . . . ?
C19 C6 C7 C8 172.6(2) . . . . ?
C19 C20 C21 C22 -1.1(4) . . . . ?
C20 C19 C24 C23 -1.3(3) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C21 C22 C23 C24 1.0(4) . . . . ?
C22 C23 C24 C19 -0.2(4) . . . . ?
C24 C19 C20 C21 2.0(3) . . . . ?
C25 C9 C10 C1 -9.6(3) . . . . ?
C25 C9 C10 C5 172.6(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 1.139
_oxdiff_exptl_absorpt_empirical_full_min 0.915
####################################################################### 
# 
# 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_sy149abs
_database_code_depnum_ccdc_archive 'CCDC 2069106'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 downloaded from the CCDC.
;
_audit_creation_date             2019-09-25
_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-hydroxy-1,1-dimethyl-5,6-diphenyl-1,2-dihydrobenzo[cd]indol-1-ium monomalonate,
;
_chemical_formula_moiety         'C25 H22 N O, C3 H3 O4'
_chemical_formula_sum            'C28 H25 N O5'
_chemical_formula_weight         455.49
_chemical_melting_point          441-444
_chemical_oxdiff_formula         'C25 O2 N1 H21'
_chemical_oxdiff_usercomment     'Colourless 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'
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                   6.0395(3)
_cell_length_b                   13.8019(8)
_cell_length_c                   14.6137(9)
_cell_angle_alpha                67.400(5)
_cell_angle_beta                 86.108(4)
_cell_angle_gamma                81.742(4)
_cell_volume                     1112.84(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5015
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      30.2800
_cell_measurement_theta_min      3.5580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.968
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 4 0 0.0981
-8 -4 2 0.0863
-1 -11 -20 0.0788
1 11 20 0.0505
1 -14 7 0.0167
1 -12 -19 0.0768
0 5 -16 0.0383
-1 15 -6 0.0362

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate / DCM'
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.055
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
8.0000 4.0000 -0.0001 -0.5976 0.7141 -0.1745
-8.0000 -4.0000 2.0001 0.6363 -0.6743 0.2639
-1.0000 -11.0000 -19.9999 0.1826 -0.1793 -0.9596
1.0000 11.0000 19.9999 -0.1826 0.1793 0.9596
1.0000 -14.0000 7.0001 0.7443 0.6529 0.1691
1.0000 -12.0000 -18.9999 0.1468 0.0776 -0.9754
-0.0000 5.0000 -16.0001 -0.5454 -0.4644 -0.6727
-1.0000 15.0000 -6.0002 -0.7721 -0.6623 -0.1161

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23808
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.889
_diffrn_reflns_theta_min         3.224
_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 0.904
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00   0.00   1.00   35.00    --  -19.97 -65.00-139.19   86
  2  ω    -86.00   0.00   1.00   35.00    --  -19.97 -65.00  95.48   86
  3  ω    -87.00   0.00   1.00   35.00    --  -19.97 -64.00 166.72   87
  4  ω      1.00  87.00   1.00   35.00    --   20.05  63.00 179.03   86
  5  ω    -51.00  49.00   1.00   35.00    --   20.05 -19.00 -90.00  100
  6  ω    -47.00  36.00   1.00   35.00    --   20.05 -55.00-139.48   83
  7  ω      3.00  87.00   1.00   35.00    --   20.05  57.00   0.00   84
  8  φ     62.00 101.00   1.00   35.00  20.05  20.05  40.00    --    39
  9  ω      0.00  87.00   1.00   35.00    --   20.05  65.00  81.02   87
 10  ω    -47.00   8.00   1.00   35.00    --   20.05 -63.00 151.56   55
 11  ω    -46.00  40.00   1.00   35.00    --   20.05 -65.00  78.71   86
;
_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      -0.0511286000
_diffrn_orient_matrix_UB_12      -0.0471413000
_diffrn_orient_matrix_UB_13      0.0193553000
_diffrn_orient_matrix_UB_21      0.1039004000
_diffrn_orient_matrix_UB_22      -0.0292785000
_diffrn_orient_matrix_UB_23      0.0198735000
_diffrn_orient_matrix_UB_31      -0.0260134000
_diffrn_orient_matrix_UB_32      0.0083935000
_diffrn_orient_matrix_UB_33      0.0446647000
_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                4061
_reflns_number_total             6361
_reflns_odcompleteness_completeness 99.78
_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         0.441
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         6361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.038
_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)+(0.0545P)²+0.5012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1563
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.c 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)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_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 0.7222(2) 0.40485(11) 0.39464(11) 0.0298(3) Uani 1 1 d . . . . .
H1 H 0.816972 0.354851 0.422637 0.045 Uiso 1 1 calc GR . . . .
N1 N 0.5324(3) 0.33370(12) 0.29473(12) 0.0220(3) Uani 1 1 d . . . . .
C1 C 0.3839(3) 0.41902(14) 0.22160(14) 0.0202(4) Uani 1 1 d . . . . .
C2 C 0.3528(3) 0.43557(15) 0.12550(14) 0.0226(4) Uani 1 1 d . . . . .
H2 H 0.434992 0.394024 0.094646 0.027 Uiso 1 1 calc R . . . .
C3 C 0.1881(3) 0.51979(15) 0.07513(14) 0.0223(4) Uani 1 1 d . . . . .
H3 H 0.164134 0.533381 0.008887 0.027 Uiso 1 1 calc R . . . .
C4 C 0.0593(3) 0.58370(14) 0.11755(13) 0.0191(4) Uani 1 1 d . . . . .
C5 C 0.1026(3) 0.56944(14) 0.21788(13) 0.0183(4) Uani 1 1 d . . . . .
C6 C 0.0088(3) 0.62926(14) 0.27597(14) 0.0201(4) Uani 1 1 d . . . . .
C7 C 0.0783(3) 0.59833(15) 0.37245(14) 0.0228(4) Uani 1 1 d . . . . .
H7 H 0.012892 0.636972 0.409437 0.027 Uiso 1 1 calc R . . . .
C8 C 0.2416(3) 0.51216(15) 0.41808(14) 0.0234(4) Uani 1 1 d . . . . .
H8 H 0.283088 0.494368 0.483248 0.028 Uiso 1 1 calc R . . . .
C9 C 0.3369(3) 0.45574(14) 0.36414(14) 0.0211(4) Uani 1 1 d . . . . .
C10 C 0.2679(3) 0.48407(14) 0.26670(13) 0.0193(4) Uani 1 1 d . . . . .
C11 C 0.7634(3) 0.32033(17) 0.25540(16) 0.0293(5) Uani 1 1 d . . . . .
H11A H 0.760380 0.297305 0.201360 0.044 Uiso 1 1 calc GR . . . .
H11B H 0.856095 0.268428 0.306982 0.044 Uiso 1 1 calc GR . . . .
H11C H 0.823025 0.386626 0.232465 0.044 Uiso 1 1 calc GR . . . .
C12 C 0.4336(4) 0.23189(15) 0.32666(15) 0.0276(4) Uani 1 1 d . . . . .
H12A H 0.285986 0.240688 0.353491 0.041 Uiso 1 1 calc GR . . . .
H12B H 0.526044 0.177178 0.376354 0.041 Uiso 1 1 calc GR . . . .
H12C H 0.425591 0.212600 0.270583 0.041 Uiso 1 1 calc GR . . . .
C13 C -0.1217(3) 0.66210(14) 0.05576(14) 0.0200(4) Uani 1 1 d . . . . .
C14 C -0.0732(3) 0.73383(15) -0.03852(14) 0.0225(4) Uani 1 1 d . . . . .
H14 H 0.073631 0.733571 -0.062262 0.027 Uiso 1 1 calc R . . . .
C15 C -0.2413(3) 0.80563(15) -0.09739(14) 0.0254(4) Uani 1 1 d . . . . .
H15 H -0.206910 0.852797 -0.160287 0.030 Uiso 1 1 calc R . . . .
C16 C -0.4594(3) 0.80704(15) -0.06261(15) 0.0268(4) Uani 1 1 d . . . . .
H16 H -0.572326 0.855127 -0.101852 0.032 Uiso 1 1 calc R . . . .
C17 C -0.5093(3) 0.73636(16) 0.03115(15) 0.0254(4) Uani 1 1 d . . . . .
H17 H -0.655888 0.737823 0.055129 0.031 Uiso 1 1 calc R . . . .
C18 C -0.3424(3) 0.66357(15) 0.08940(14) 0.0214(4) Uani 1 1 d . . . . .
H18 H -0.378349 0.615295 0.151506 0.026 Uiso 1 1 calc R . . . .
C19 C -0.1615(3) 0.72523(15) 0.24021(14) 0.0210(4) Uani 1 1 d . . . . .
C20 C -0.1157(3) 0.81809(15) 0.16302(15) 0.0258(4) Uani 1 1 d . . . . .
H20 H 0.024113 0.821273 0.131862 0.031 Uiso 1 1 calc R . . . .
C21 C -0.2769(4) 0.90559(17) 0.13244(17) 0.0350(5) Uani 1 1 d . . . . .
H21 H -0.245615 0.967070 0.080373 0.042 Uiso 1 1 calc R . . . .
C22 C -0.4851(4) 0.90200(18) 0.17915(18) 0.0389(6) Uani 1 1 d . . . . .
H22 H -0.593750 0.960706 0.158165 0.047 Uiso 1 1 calc R . . . .
C23 C -0.5301(4) 0.81100(18) 0.25682(17) 0.0338(5) Uani 1 1 d . . . . .
H23 H -0.669080 0.808473 0.288597 0.041 Uiso 1 1 calc R . . . .
C24 C -0.3687(3) 0.72332(16) 0.28765(15) 0.0268(4) Uani 1 1 d . . . . .
H24 H -0.399650 0.662539 0.340693 0.032 Uiso 1 1 calc R . . . .
C25 C 0.5279(3) 0.36793(15) 0.38928(14) 0.0222(4) Uani 1 1 d . . . . .
H25 H 0.497620 0.309290 0.450969 0.027 Uiso 1 1 calc R . . . .
O2 O 0.2103(3) 0.86505(14) 0.48166(13) 0.0471(5) Uani 1 1 d . . . . .
O3 O -0.0284(3) 0.74731(12) 0.51187(11) 0.0344(4) Uani 1 1 d . . . . .
O4 O 0.1324(3) 1.04360(14) 0.34886(14) 0.0529(5) Uani 1 1 d . . . . .
H4 H 0.191528 0.991814 0.394218 0.079 Uiso 1 1 calc GR . . . .
O5 O -0.1712(3) 1.08610(13) 0.26014(13) 0.0486(5) Uani 1 1 d . . . . .
C26 C 0.0284(4) 0.83772(18) 0.46870(16) 0.0306(5) Uani 1 1 d . . . . .
C27 C -0.1372(4) 0.91983(18) 0.39548(19) 0.0400(6) Uani 1 1 d . . . . .
H27A H -0.187398 0.887491 0.353565 0.048 Uiso 1 1 calc R . . . .
H27B H -0.266535 0.935211 0.433065 0.048 Uiso 1 1 calc R . . . .
C28 C -0.0614(4) 1.02377(18) 0.32879(17) 0.0355(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C25 1.363(2) . ?
N1 C1 1.481(2) . ?
N1 C11 1.487(3) . ?
N1 C12 1.499(2) . ?
N1 C25 1.621(2) . ?
C1 C2 1.355(3) . ?
C1 C10 1.394(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.412(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C4 C5 1.440(2) . ?
C4 C13 1.491(2) . ?
C5 C6 1.436(3) . ?
C5 C10 1.416(2) . ?
C6 C7 1.383(3) . ?
C6 C19 1.495(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.405(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.357(3) . ?
C9 C10 1.400(3) . ?
C9 C25 1.499(3) . ?
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 1.394(3) . ?
C13 C18 1.389(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.393(3) . ?
C19 C24 1.388(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.387(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.378(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.385(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9800 . ?
O2 C26 1.260(3) . ?
O3 C26 1.249(3) . ?
O4 H4 0.8200 . ?
O4 C28 1.315(3) . ?
O5 C28 1.204(3) . ?
C26 C27 1.522(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.507(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
C25 O1 H1 109.5 . . ?
C1 N1 C11 112.58(15) . . ?
C1 N1 C12 109.34(14) . . ?
C1 N1 C25 104.78(14) . . ?
C11 N1 C12 110.00(15) . . ?
C11 N1 C25 111.80(14) . . ?
C12 N1 C25 108.13(14) . . ?
C2 C1 N1 128.41(17) . . ?
C2 C1 C10 122.13(17) . . ?
C10 C1 N1 109.45(15) . . ?
C1 C2 H2 122.1 . . ?
C1 C2 C3 115.86(17) . . ?
C3 C2 H2 122.1 . . ?
C2 C3 H3 117.7 . . ?
C4 C3 C2 124.57(17) . . ?
C4 C3 H3 117.7 . . ?
C3 C4 C5 119.07(17) . . ?
C3 C4 C13 116.98(16) . . ?
C5 C4 C13 123.93(16) . . ?
C6 C5 C4 130.42(17) . . ?
C10 C5 C4 114.97(16) . . ?
C10 C5 C6 114.59(16) . . ?
C5 C6 C19 124.96(16) . . ?
C7 C6 C5 119.20(17) . . ?
C7 C6 C19 115.84(16) . . ?
C6 C7 H7 117.9 . . ?
C6 C7 C8 124.10(18) . . ?
C8 C7 H7 117.9 . . ?
C7 C8 H8 121.0 . . ?
C9 C8 C7 117.94(17) . . ?
C9 C8 H8 121.0 . . ?
C8 C9 C10 119.37(18) . . ?
C8 C9 C25 129.67(17) . . ?
C10 C9 C25 110.75(17) . . ?
C1 C10 C5 123.21(16) . . ?
C1 C10 C9 112.03(17) . . ?
C9 C10 C5 124.76(17) . . ?
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 120.43(17) . . ?
C18 C13 C4 121.01(17) . . ?
C18 C13 C14 118.55(17) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.83(19) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.02(18) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.62(18) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.45(19) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.52(18) . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C6 122.00(18) . . ?
C24 C19 C6 119.13(17) . . ?
C24 C19 C20 118.83(18) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.7(2) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.7(2) . . ?
C23 C24 H24 119.7 . . ?
O1 C25 N1 110.92(15) . . ?
O1 C25 C9 110.51(15) . . ?
O1 C25 H25 111.2 . . ?
N1 C25 H25 111.2 . . ?
C9 C25 N1 101.46(14) . . ?
C9 C25 H25 111.2 . . ?
C28 O4 H4 109.5 . . ?
O2 C26 C27 118.5(2) . . ?
O3 C26 O2 124.9(2) . . ?
O3 C26 C27 116.65(19) . . ?
C26 C27 H27A 107.7 . . ?
C26 C27 H27B 107.7 . . ?
H27A C27 H27B 107.1 . . ?
C28 C27 C26 118.6(2) . . ?
C28 C27 H27A 107.7 . . ?
C28 C27 H27B 107.7 . . ?
O4 C28 C27 116.8(2) . . ?
O5 C28 O4 121.1(2) . . ?
O5 C28 C27 122.1(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 175.79(17) . . . . ?
N1 C1 C10 C5 -176.19(16) . . . . ?
N1 C1 C10 C9 4.7(2) . . . . ?
C1 N1 C25 O1 -105.37(16) . . . . ?
C1 N1 C25 C9 12.03(17) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C1 C10 C5 2.7(3) . . . . ?
C2 C1 C10 C9 -176.39(17) . . . . ?
C2 C3 C4 C5 4.2(3) . . . . ?
C2 C3 C4 C13 -174.29(17) . . . . ?
C3 C4 C5 C6 174.30(18) . . . . ?
C3 C4 C5 C10 -4.2(2) . . . . ?
C3 C4 C13 C14 -54.1(2) . . . . ?
C3 C4 C13 C18 124.18(19) . . . . ?
C4 C5 C6 C7 179.48(18) . . . . ?
C4 C5 C6 C19 -0.9(3) . . . . ?
C4 C5 C10 C1 1.0(3) . . . . ?
C4 C5 C10 C9 179.94(17) . . . . ?
C4 C13 C14 C15 178.65(17) . . . . ?
C4 C13 C18 C17 -179.64(16) . . . . ?
C5 C4 C13 C14 127.54(19) . . . . ?
C5 C4 C13 C18 -54.2(2) . . . . ?
C5 C6 C7 C8 1.6(3) . . . . ?
C5 C6 C19 C20 -63.7(2) . . . . ?
C5 C6 C19 C24 118.8(2) . . . . ?
C6 C5 C10 C1 -177.74(17) . . . . ?
C6 C5 C10 C9 1.2(3) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C6 C19 C20 C21 -179.50(18) . . . . ?
C6 C19 C24 C23 179.67(17) . . . . ?
C7 C6 C19 C20 115.9(2) . . . . ?
C7 C6 C19 C24 -61.6(2) . . . . ?
C7 C8 C9 C10 -0.9(3) . . . . ?
C7 C8 C9 C25 173.46(18) . . . . ?
C8 C9 C10 C1 179.31(17) . . . . ?
C8 C9 C10 C5 0.2(3) . . . . ?
C8 C9 C25 O1 -66.9(3) . . . . ?
C8 C9 C25 N1 175.41(19) . . . . ?
C10 C1 C2 C3 -2.9(3) . . . . ?
C10 C5 C6 C7 -2.1(2) . . . . ?
C10 C5 C6 C19 177.57(16) . . . . ?
C10 C9 C25 O1 107.82(18) . . . . ?
C10 C9 C25 N1 -9.88(19) . . . . ?
C11 N1 C1 C2 48.9(3) . . . . ?
C11 N1 C1 C10 -132.29(17) . . . . ?
C11 N1 C25 O1 16.8(2) . . . . ?
C11 N1 C25 C9 134.25(16) . . . . ?
C12 N1 C1 C2 -73.7(2) . . . . ?
C12 N1 C1 C10 105.12(17) . . . . ?
C12 N1 C25 O1 138.09(16) . . . . ?
C12 N1 C25 C9 -104.51(16) . . . . ?
C13 C4 C5 C6 -7.3(3) . . . . ?
C13 C4 C5 C10 174.22(16) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C13 C18 C17 -1.4(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
C16 C17 C18 C13 1.7(3) . . . . ?
C18 C13 C14 C15 0.4(3) . . . . ?
C19 C6 C7 C8 -178.06(17) . . . . ?
C19 C20 C21 C22 0.7(3) . . . . ?
C20 C19 C24 C23 2.1(3) . . . . ?
C20 C21 C22 C23 0.5(3) . . . . ?
C21 C22 C23 C24 -0.4(3) . . . . ?
C22 C23 C24 C19 -0.9(3) . . . . ?
C24 C19 C20 C21 -2.0(3) . . . . ?
C25 N1 C1 C2 170.63(18) . . . . ?
C25 N1 C1 C10 -10.58(19) . . . . ?
C25 C9 C10 C1 4.0(2) . . . . ?
C25 C9 C10 C5 -175.09(17) . . . . ?
O2 C26 C27 C28 10.6(3) . . . . ?
O3 C26 C27 C28 -169.5(2) . . . . ?
C26 C27 C28 O4 -10.5(3) . . . . ?
C26 C27 C28 O5 169.4(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 1.103
_oxdiff_exptl_absorpt_empirical_full_min 0.918


####################################################################### 
# 
# 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_jb431filter
_database_code_depnum_ccdc_archive 'CCDC 2069105'
loop_
_audit_author_name
_audit_author_address
'John Wallis'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2021-03-09 deposited with the CCDC.	2021-05-27 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-hydroxy-1,1-dimethyl-5,6-diphenyl-1,2-dihydrobenzo[cd]indol-1-ium chloride
;
_chemical_formula_moiety         'Cl, C H2 Cl2, C25 H22 N O'
_chemical_formula_sum            'C26 H24 Cl3 N O'
_chemical_formula_weight         472.81
_chemical_absolute_configuration ad
_chemical_melting_point          '423 dec.'
_chemical_oxdiff_formula         'C25 H22 O1 N1 Cl1'
_chemical_oxdiff_usercomment     'Colourless 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'
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.1138(3)
_cell_length_b                   11.1707(5)
_cell_length_c                   33.8350(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2310.78(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3212
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      27.0330
_cell_measurement_theta_min      2.5660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.901
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 5 45 0.0363
0 -5 -45 0.0378
6 -11 12 0.1540
-6 11 -16 0.1268
-1 16 -2 0.0551
1 -16 2 0.0551
8 1 -12 0.1864
-8 -1 12 0.1864
-1 -15 5 0.0546

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.074
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
-0.0177 4.9784 45.0139 -0.9154 -0.1845 -0.3416
0.0177 -4.9784 -45.0139 0.9154 0.1845 0.3416
5.9974 -11.0065 12.0043 -0.3616 -0.0466 0.9504
-5.9960 11.0085 -16.0051 0.4379 0.0801 -0.9419
-1.0056 16.0046 -1.9880 -0.1011 0.5542 -0.8553
1.0056 -16.0046 1.9880 0.1011 -0.5542 0.8553
7.9996 1.0094 -11.9862 -0.1265 0.7770 0.5561
-7.9996 -1.0094 11.9862 0.1265 -0.7770 -0.5561
-0.9948 -15.0066 4.9857 0.1185 -0.7003 0.6547

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            15877
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_min         2.185
_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 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  49.00   1.00   30.00    --  -19.89  37.00 -30.00   88
  2  ω     35.00  92.00   1.00   30.00    --   20.05 178.00-120.00   57
  3  ω     -9.00  91.00   1.00   30.00    --   20.05  19.00  60.00  100
  4  ω     32.00  87.00   1.00   30.00    --   20.05-178.00 120.00   55
;
_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      -0.0429832000
_diffrn_orient_matrix_UB_12      -0.0113918000
_diffrn_orient_matrix_UB_13      -0.0190938000
_diffrn_orient_matrix_UB_21      0.0797658000
_diffrn_orient_matrix_UB_22      0.0386066000
_diffrn_orient_matrix_UB_23      -0.0083365000
_diffrn_orient_matrix_UB_31      0.0725341000
_diffrn_orient_matrix_UB_32      -0.0491450000
_diffrn_orient_matrix_UB_33      -0.0021254000
_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         0.730
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4042
_reflns_number_total             5702
_reflns_odcompleteness_completeness 99.85
_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         0.492
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1156 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5702
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0594
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+0.1274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1217
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B)
2.c 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)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
Cl1 Cl 0.68983(17) 0.50784(9) 0.21853(3) 0.0324(2) Uani 1 1 d . . . . .
Cl2 Cl 0.7980(2) 1.01206(12) 0.34858(4) 0.0607(4) Uani 1 1 d . . . . .
Cl3 Cl 1.1725(3) 1.03672(15) 0.40178(4) 0.0879(6) Uani 1 1 d . . . . .
C26 C 1.0400(8) 0.9470(4) 0.36709(14) 0.0382(11) Uani 1 1 d . . . . .
H26A H 1.004648 0.870720 0.379184 0.046 Uiso 1 1 calc R . . . .
H26B H 1.138866 0.931721 0.345251 0.046 Uiso 1 1 calc R . . . .
O1 O -0.0792(5) 0.5544(3) 0.29261(10) 0.0450(9) Uani 1 1 d . . . . .
H1 H -0.157540 0.552978 0.272938 0.067 Uiso 1 1 calc GR . . . .
N1 N 0.1629(5) 0.3785(3) 0.28981(9) 0.0230(7) Uani 1 1 d . . . . .
C1 C 0.3133(7) 0.3710(3) 0.32374(11) 0.0225(8) Uani 1 1 d . . . . .
C2 C 0.3830(7) 0.2723(4) 0.34289(12) 0.0255(9) Uani 1 1 d . . . . .
H2 H 0.341444 0.195851 0.335026 0.031 Uiso 1 1 calc R . . . .
C3 C 0.5223(7) 0.2914(4) 0.37552(12) 0.0275(10) Uani 1 1 d . . . . .
H3 H 0.570372 0.224687 0.389479 0.033 Uiso 1 1 calc R . . . .
C4 C 0.5921(6) 0.4028(4) 0.38811(12) 0.0229(9) Uani 1 1 d . . . . .
C5 C 0.5272(6) 0.5072(4) 0.36613(11) 0.0209(8) Uani 1 1 d . . . . .
C6 C 0.5842(6) 0.6307(4) 0.37146(12) 0.0224(9) Uani 1 1 d . . . . .
C7 C 0.4907(7) 0.7160(4) 0.34704(12) 0.0272(10) Uani 1 1 d . . . . .
H7 H 0.529380 0.795560 0.351034 0.033 Uiso 1 1 calc R . . . .
C8 C 0.3415(7) 0.6904(4) 0.31667(12) 0.0279(9) Uani 1 1 d . . . . .
H8 H 0.280250 0.750904 0.301385 0.034 Uiso 1 1 calc R . . . .
C9 C 0.2904(7) 0.5736(3) 0.31053(11) 0.0247(9) Uani 1 1 d . . . . .
C10 C 0.3823(6) 0.4856(3) 0.33439(11) 0.0214(8) Uani 1 1 d . . . . .
C11 C -0.0466(7) 0.3151(4) 0.29818(13) 0.0364(11) Uani 1 1 d . . . . .
H11A H -0.019305 0.230857 0.300775 0.055 Uiso 1 1 calc GR . . . .
H11B H -0.147184 0.328540 0.276843 0.055 Uiso 1 1 calc GR . . . .
H11C H -0.108355 0.345154 0.322312 0.055 Uiso 1 1 calc GR . . . .
C12 C 0.2649(7) 0.3254(4) 0.25352(11) 0.0316(10) Uani 1 1 d . . . . .
H12A H 0.393188 0.370267 0.246590 0.047 Uiso 1 1 calc GR . . . .
H12B H 0.162097 0.328187 0.232096 0.047 Uiso 1 1 calc GR . . . .
H12C H 0.304690 0.243719 0.258651 0.047 Uiso 1 1 calc GR . . . .
C13 C 0.7289(6) 0.4029(3) 0.42463(12) 0.0241(9) Uani 1 1 d . . . . .
C14 C 0.9256(7) 0.3404(4) 0.42502(14) 0.0343(11) Uani 1 1 d . . . . .
H14 H 0.972815 0.301122 0.402339 0.041 Uiso 1 1 calc R . . . .
C15 C 1.0507(8) 0.3363(5) 0.45883(15) 0.0430(13) Uani 1 1 d . . . . .
H15 H 1.183164 0.295415 0.458635 0.052 Uiso 1 1 calc R . . . .
C16 C 0.9818(9) 0.3922(5) 0.49301(15) 0.0446(13) Uani 1 1 d . . . . .
H16 H 1.066398 0.388722 0.515823 0.054 Uiso 1 1 calc R . . . .
C17 C 0.7873(9) 0.4529(4) 0.49288(13) 0.0391(11) Uani 1 1 d . . . . .
H17 H 0.739825 0.490858 0.515796 0.047 Uiso 1 1 calc R . . . .
C18 C 0.6604(7) 0.4586(4) 0.45904(12) 0.0297(10) Uani 1 1 d . . . . .
H18 H 0.528467 0.499949 0.459419 0.036 Uiso 1 1 calc R . . . .
C19 C 0.7438(6) 0.6755(3) 0.40130(11) 0.0219(9) Uani 1 1 d . . . . .
C20 C 0.9558(7) 0.6312(4) 0.40345(12) 0.0269(9) Uani 1 1 d . . . . .
H20 H 1.001343 0.572255 0.385862 0.032 Uiso 1 1 calc R . . . .
C21 C 1.0985(7) 0.6741(4) 0.43152(13) 0.0309(10) Uani 1 1 d . . . . .
H21 H 1.238809 0.642231 0.433036 0.037 Uiso 1 1 calc R . . . .
C22 C 1.0383(8) 0.7630(4) 0.45731(14) 0.0355(11) Uani 1 1 d . . . . .
H22 H 1.136349 0.790832 0.476213 0.043 Uiso 1 1 calc R . . . .
C23 C 0.8293(8) 0.8108(4) 0.45482(12) 0.0319(10) Uani 1 1 d . . . . .
H23 H 0.787006 0.872380 0.471673 0.038 Uiso 1 1 calc R . . . .
C24 C 0.6840(7) 0.7663(3) 0.42706(12) 0.0268(9) Uani 1 1 d . . . . .
H24 H 0.543471 0.797911 0.425677 0.032 Uiso 1 1 calc R . . . .
C25 C 0.1269(6) 0.5202(3) 0.28260(12) 0.0249(9) Uani 1 1 d . . . . .
H25 H 0.160296 0.542039 0.255204 0.030 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2 C26 1.763(5) . ?
Cl3 C26 1.743(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
O1 H1 0.8200 . ?
O1 C25 1.360(4) . ?
N1 C1 1.473(5) . ?
N1 C11 1.491(5) . ?
N1 C12 1.499(5) . ?
N1 C25 1.617(5) . ?
C1 C2 1.347(5) . ?
C1 C10 1.396(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.411(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(6) . ?
C4 C5 1.439(5) . ?
C4 C13 1.492(5) . ?
C5 C6 1.434(5) . ?
C5 C10 1.413(5) . ?
C6 C7 1.384(6) . ?
C6 C19 1.491(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.404(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.357(5) . ?
C9 C10 1.391(5) . ?
C9 C25 1.499(5) . ?
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 1.390(6) . ?
C13 C18 1.385(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.369(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.389(5) . ?
C19 C24 1.386(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.372(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.388(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.385(6) . ?
C24 H24 0.9300 . ?
C25 H25 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
Cl2 C26 H26A 109.0 . . ?
Cl2 C26 H26B 109.0 . . ?
Cl3 C26 Cl2 113.1(3) . . ?
Cl3 C26 H26A 109.0 . . ?
Cl3 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
C25 O1 H1 109.5 . . ?
C1 N1 C11 111.2(3) . . ?
C1 N1 C12 110.9(3) . . ?
C1 N1 C25 105.0(3) . . ?
C11 N1 C12 109.0(3) . . ?
C11 N1 C25 112.1(3) . . ?
C12 N1 C25 108.7(3) . . ?
C2 C1 N1 128.2(4) . . ?
C2 C1 C10 122.0(4) . . ?
C10 C1 N1 109.7(3) . . ?
C1 C2 H2 121.8 . . ?
C1 C2 C3 116.3(4) . . ?
C3 C2 H2 121.8 . . ?
C2 C3 H3 117.9 . . ?
C4 C3 C2 124.3(4) . . ?
C4 C3 H3 117.9 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 C13 115.4(3) . . ?
C5 C4 C13 125.6(3) . . ?
C6 C5 C4 130.3(4) . . ?
C10 C5 C4 115.3(3) . . ?
C10 C5 C6 114.3(3) . . ?
C5 C6 C19 124.6(4) . . ?
C7 C6 C5 119.1(4) . . ?
C7 C6 C19 116.3(4) . . ?
C6 C7 H7 117.8 . . ?
C6 C7 C8 124.4(4) . . ?
C8 C7 H7 117.8 . . ?
C7 C8 H8 121.4 . . ?
C9 C8 C7 117.2(4) . . ?
C9 C8 H8 121.4 . . ?
C8 C9 C10 119.8(4) . . ?
C8 C9 C25 129.2(4) . . ?
C10 C9 C25 110.7(3) . . ?
C1 C10 C5 122.9(4) . . ?
C9 C10 C1 112.1(3) . . ?
C9 C10 C5 125.0(4) . . ?
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 119.5(4) . . ?
C18 C13 C4 121.8(4) . . ?
C18 C13 C14 118.6(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.8(5) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.1(4) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.8(4) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.4(4) . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C6 121.8(4) . . ?
C24 C19 C6 119.9(4) . . ?
C24 C19 C20 118.3(4) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(4) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.3 . . ?
C22 C21 C20 121.4(4) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 H22 120.4 . . ?
C21 C22 C23 119.1(4) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.6(4) . . ?
C24 C23 H23 120.2 . . ?
C19 C24 H24 119.3 . . ?
C23 C24 C19 121.3(4) . . ?
C23 C24 H24 119.3 . . ?
O1 C25 N1 111.3(3) . . ?
O1 C25 C9 110.4(3) . . ?
O1 C25 H25 111.0 . . ?
N1 C25 H25 111.0 . . ?
C9 C25 N1 101.8(3) . . ?
C9 C25 H25 111.0 . . ?

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 -177.9(4) . . . . ?
N1 C1 C10 C5 179.7(3) . . . . ?
N1 C1 C10 C9 0.3(4) . . . . ?
C1 N1 C25 O1 -109.9(3) . . . . ?
C1 N1 C25 C9 7.7(4) . . . . ?
C1 C2 C3 C4 -1.1(6) . . . . ?
C2 C1 C10 C5 -0.8(6) . . . . ?
C2 C1 C10 C9 179.8(4) . . . . ?
C2 C3 C4 C5 -2.4(6) . . . . ?
C2 C3 C4 C13 176.7(4) . . . . ?
C3 C4 C5 C6 -176.6(4) . . . . ?
C3 C4 C5 C10 4.1(5) . . . . ?
C3 C4 C13 C14 60.0(5) . . . . ?
C3 C4 C13 C18 -116.6(4) . . . . ?
C4 C5 C6 C7 -177.1(4) . . . . ?
C4 C5 C6 C19 4.4(6) . . . . ?
C4 C5 C10 C1 -2.7(5) . . . . ?
C4 C5 C10 C9 176.7(4) . . . . ?
C4 C13 C14 C15 -178.0(4) . . . . ?
C4 C13 C18 C17 177.4(4) . . . . ?
C5 C4 C13 C14 -121.0(4) . . . . ?
C5 C4 C13 C18 62.4(6) . . . . ?
C5 C6 C7 C8 -0.2(6) . . . . ?
C5 C6 C19 C20 54.3(5) . . . . ?
C5 C6 C19 C24 -127.6(4) . . . . ?
C6 C5 C10 C1 177.9(3) . . . . ?
C6 C5 C10 C9 -2.7(5) . . . . ?
C6 C7 C8 C9 -1.5(7) . . . . ?
C6 C19 C20 C21 -179.6(4) . . . . ?
C6 C19 C24 C23 -179.3(4) . . . . ?
C7 C6 C19 C20 -124.2(4) . . . . ?
C7 C6 C19 C24 53.9(5) . . . . ?
C7 C8 C9 C10 1.1(6) . . . . ?
C7 C8 C9 C25 175.3(4) . . . . ?
C8 C9 C10 C1 -179.5(4) . . . . ?
C8 C9 C10 C5 1.1(6) . . . . ?
C8 C9 C25 O1 -64.2(6) . . . . ?
C8 C9 C25 N1 177.5(4) . . . . ?
C10 C1 C2 C3 2.7(6) . . . . ?
C10 C5 C6 C7 2.2(5) . . . . ?
C10 C5 C6 C19 -176.3(3) . . . . ?
C10 C9 C25 O1 110.4(4) . . . . ?
C10 C9 C25 N1 -7.9(4) . . . . ?
C11 N1 C1 C2 53.9(6) . . . . ?
C11 N1 C1 C10 -126.7(4) . . . . ?
C11 N1 C25 O1 10.9(4) . . . . ?
C11 N1 C25 C9 128.6(3) . . . . ?
C12 N1 C1 C2 -67.5(5) . . . . ?
C12 N1 C1 C10 111.9(4) . . . . ?
C12 N1 C25 O1 131.4(3) . . . . ?
C12 N1 C25 C9 -110.9(3) . . . . ?
C13 C4 C5 C6 4.4(7) . . . . ?
C13 C4 C5 C10 -174.9(4) . . . . ?
C13 C14 C15 C16 1.1(7) . . . . ?
C14 C13 C18 C17 0.8(6) . . . . ?
C14 C15 C16 C17 -0.5(8) . . . . ?
C15 C16 C17 C18 0.0(7) . . . . ?
C16 C17 C18 C13 -0.2(7) . . . . ?
C18 C13 C14 C15 -1.2(6) . . . . ?
C19 C6 C7 C8 178.4(4) . . . . ?
C19 C20 C21 C22 -1.6(6) . . . . ?
C20 C19 C24 C23 -1.1(6) . . . . ?
C20 C21 C22 C23 -0.3(7) . . . . ?
C21 C22 C23 C24 1.5(6) . . . . ?
C22 C23 C24 C19 -0.7(6) . . . . ?
C24 C19 C20 C21 2.3(6) . . . . ?
C25 N1 C1 C2 175.4(4) . . . . ?
C25 N1 C1 C10 -5.2(4) . . . . ?
C25 C9 C10 C1 5.3(4) . . . . ?
C25 C9 C10 C5 -174.1(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 1.102
_oxdiff_exptl_absorpt_empirical_full_min 0.839
