# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

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

data_exp_49_autored
_database_code_depnum_ccdc_archive 'CCDC 2382169'
loop_
_audit_author_name
_audit_author_address
'takahiro sawano'
;Shimane University
Japan
;
_audit_update_record             
;
2024-09-06 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;
_audit_creation_date             2024-08-29
_audit_creation_method           
;
Olex2 1.5-ac6-017
(compiled 2024.02.01 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6920)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
7-Bromo-3-(2-phenylpenta-3,4-dien-2-yl)-1H-indole
_chemical_formula_moiety         'C19 H16 Br N'
_chemical_formula_sum            'C19 H16 Br N'
_chemical_formula_weight         338.24
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H16N1Br1
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'
Br Br -0.6763 1.2805 '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      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                   8.52880(10)
_cell_length_b                   6.05890(10)
_cell_length_c                   14.83580(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.3240(10)
_cell_angle_gamma                90
_cell_volume                     766.630(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13705
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.9540
_cell_measurement_theta_min      2.9670
_shelx_estimated_absorpt_T_max   0.616
_shelx_estimated_absorpt_T_min   0.457
_exptl_absorpt_coefficient_mu    3.572
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.340
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.108a (Rigaku Oxford Diffraction, 2024)
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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -3 6 0.0713
-5 -1 -2 0.0919
5 2 -1 0.0481
3 -3 4 0.0875
-2 0 -9 0.1190
-5 -1 -1 0.0851
5 2 -3 0.0475
-3 -3 -2 0.0953
-1 3 6 0.0934
-3 2 -7 0.1198
2 0 9 0.0799
2 -2 -7 0.1009

_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
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
-1.5347 -2.8074 6.2072 -0.3890 -0.6436 0.6592
-5.2006 -1.0647 -1.9877 -0.4521 -0.7359 -0.5041
4.8236 1.9148 -0.6833 0.5144 0.8412 0.1670
2.8669 -2.9642 3.8636 0.3402 -0.3157 0.8858
-2.0460 0.1327 -8.9224 0.3159 -0.3048 -0.8985
-5.4526 -0.5963 -0.7806 -0.5998 -0.6377 -0.4832
4.7056 1.6260 -3.1968 0.6871 0.7265 -0.0093
-3.0648 -3.1832 -1.8655 -0.0240 -0.9972 -0.0706
-0.7507 3.0280 6.0111 -0.7249 0.6850 0.0723
-2.7286 1.8268 -7.0569 -0.0246 0.0299 -0.9992
1.7501 -0.1038 9.1155 -0.3687 0.2873 0.8841
2.1782 -2.3909 -6.6614 0.9013 -0.4283 -0.0658

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15912
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.162
_diffrn_reflns_theta_min         2.979
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     44.00 105.00   0.50    0.05    --  117.50 -95.00-180.00  122
  2  ω     46.00 111.00   0.50    0.05    --  117.50-125.00-180.00  130
  3  ω     44.00 105.00   0.50    0.05    --  117.50 -95.00 -90.00  122
  4  ω     44.00 105.00   0.50    0.05    --  117.50 -95.00-150.00  122
  5  ω     44.00 105.00   0.50    0.05    --  117.50 -95.00 -30.00  122
  6  ω     44.00 105.00   0.50    0.05    --  117.50 -95.00   0.00  122
  7  ω     46.00 111.00   0.50    0.05    --  117.50-125.00  60.00  130
  8  ω     44.00 105.00   0.50    0.05    --  117.50 -95.00 150.00  122
  9  ω    -21.00  78.00   0.50    0.05    --   43.97 -88.00  51.00  198
 10  ω     44.00 152.00   0.50    0.05    --  117.50 -88.00  51.00  216
 11  ω     44.00 152.00   0.50    0.05    --  117.50 -88.00  51.00  216
 12  ω     44.00  72.00   0.50    0.05    --  117.50 -61.00  30.00   56
 13  ω     44.00  72.00   0.50    0.05    --  117.50 -61.00  60.00   56
 14  ω     44.00  72.00   0.50    0.05    --  117.50 -61.00  90.00   56
 15  ω     44.00  72.00   0.50    0.05    --  117.50 -61.00 150.00   56
 16  ω     44.00  72.00   0.50    0.05    --  117.50 -61.00 -60.00   56
 17  ω     44.00  72.00   0.50    0.05    --  117.50 -61.00-150.00   56
 18  ω     95.00 178.00   0.50    0.05    --  117.50  45.00 -60.00  166
 19  ω     95.00 178.00   0.50    0.05    --  117.50  61.00 -90.00  166
 20  ω     95.00 178.00   0.50    0.05    --  117.50  61.00-150.00  166
 21  ω     95.00 178.00   0.50    0.05    --  117.50  61.00 -90.00  166
 22  ω     95.00 178.00   0.50    0.05    --  117.50  61.00   0.00  166
 23  ω     95.00 178.00   0.50    0.05    --  117.50  61.00   0.00  166
 24  ω     95.00 178.00   0.50    0.05    --  117.50  45.00-120.00  166
 25  ω     89.00 178.00   0.50    0.05    --  117.50  77.00  90.00  178
 26  ω     89.00 178.00   0.50    0.05    --  117.50  77.00  90.00  178
 27  ω     95.00 178.00   0.50    0.05    --  117.50  61.00 120.00  166
 28  ω    101.00 178.00   0.50    0.05    --  117.50  88.00 167.00  154
 29  ω     95.00 178.00   0.50    0.05    --  117.50 125.00 120.00  166
 30  ω     95.00 178.00   0.50    0.05    --  117.50 125.00-120.00  166
 31  ω     95.00 178.00   0.50    0.05    --  117.50 125.00-150.00  166
 32  ω     63.00 122.00   0.50    0.05    --   43.97 178.00 150.00  118
 33  ω     63.00 122.00   0.50    0.05    --   43.97 178.00  90.00  118
 34  ω      8.00  34.00   0.50    0.05    --   43.97  93.00  87.57   52
 35  ω    -23.00  37.00   0.50    0.05    --  -43.97  19.00 120.00  120
 36  ω    -23.00  37.00   0.50    0.05    --  -43.97  19.00  90.00  120
 37  ω    -23.00  37.00   0.50    0.05    --  -43.97  19.00-180.00  120
 38  ω    -50.00 -20.00   0.50    0.05    --  -96.00  45.00 -60.00   60
 39  ω   -130.00 -22.00   0.50    0.05    --  -96.00  88.00 167.00  216
 40  ω    -78.00  30.00   0.50    0.05    --  -43.97  88.00 167.00  216
 41  ω    -50.00 -20.00   0.50    0.05    --  -96.00  45.00  30.00   60
 42  ω    -50.00 -20.00   0.50    0.05    --  -96.00  45.00-180.00   60
 43  ω   -117.00 -15.00   0.50    0.05    --  -43.97 -77.00-150.00  204
 44  ω   -117.00 -15.00   0.50    0.05    --  -43.97 -77.00   0.00  204
 45  ω   -117.00 -21.00   0.50    0.05    --  -43.97 -57.00  90.00  192
 46  ω   -170.00 -74.00   0.50    0.05    --  -96.00 -56.00 -40.56  192
 47  ω   -170.00 -79.00   0.50    0.05    --  -96.00 -88.00  51.00  182
 48  ω   -170.00 -79.00   0.50    0.05    --  -96.00 -88.00  51.00  182
 49  ω   -122.00 -41.00   0.50    0.05    --  -43.97-178.00-150.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1278547000
_diffrn_orient_matrix_UB_12      -0.0769605000
_diffrn_orient_matrix_UB_13      -0.0658662000
_diffrn_orient_matrix_UB_21      0.0909725000
_diffrn_orient_matrix_UB_22      0.2160101000
_diffrn_orient_matrix_UB_23      0.0165081000
_diffrn_orient_matrix_UB_31      0.0894017000
_diffrn_orient_matrix_UB_32      -0.1099486000
_diffrn_orient_matrix_UB_33      0.0785681000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                3258
_reflns_number_total             3272
_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 1.171.43.108a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.108a 64-bit (release 14-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.108a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-017 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-017 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1444 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3272
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0176
_refine_ls_R_factor_gt           0.0176
_refine_ls_restrained_S_all      1.082
_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)+(0.0246P)²+0.2482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0467
_refine_ls_wR_factor_ref         0.0467
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N002(H002), C003(H003), C006(H006), C007(H007), C009(H009), C00B(H00B),
 C00C(H00C), C00D(H00D), C00G(H00G), C00I(H00I), C00L(H00L)
2.b Idealised Me refined as rotating group:
 C00K(H00F,H00H,H00J)
;
_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
Br01 Br 0.11182(2) 0.70166(5) 0.41863(2) 0.02239(7) Uani 1 1 d . . . . .
N002 N 0.1898(2) 0.7875(3) 0.63184(13) 0.0163(4) Uani 1 1 d . . . . .
H002 H 0.128213 0.887027 0.606928 0.020 Uiso 1 1 calc R U . . .
C003 C 0.2447(3) 0.7906(4) 0.72000(15) 0.0156(4) Uani 1 1 d . . . . .
H003 H 0.221666 0.901929 0.763004 0.019 Uiso 1 1 calc R U . . .
C004 C 0.3367(3) 0.6104(4) 0.73595(14) 0.0146(4) Uani 1 1 d . . . . .
C005 C 0.2268(2) 0.5274(4) 0.50238(15) 0.0170(4) Uani 1 1 d . . . . .
C006 C 0.2935(3) 0.3300(4) 0.47716(15) 0.0185(5) Uani 1 1 d . . . . .
H006 H 0.277296 0.275095 0.417849 0.022 Uiso 1 1 calc R U . . .
C007 C 0.4117(3) 0.2879(4) 0.62574(15) 0.0168(4) Uani 1 1 d . . . . .
H007 H 0.477198 0.208467 0.666325 0.020 Uiso 1 1 calc R U . . .
C008 C 0.3404(2) 0.4857(4) 0.65295(15) 0.0149(4) Uani 1 1 d . . . . .
C009 C 0.6697(3) 0.3245(4) 0.84370(15) 0.0185(4) Uani 1 1 d . . . . .
H009 H 0.613567 0.211576 0.874020 0.022 Uiso 1 1 calc R U . . .
C00A C 0.4127(3) 0.5425(4) 0.82502(14) 0.0150(4) Uani 1 1 d . . . . .
C00B C 0.8316(3) 0.3041(4) 0.83238(16) 0.0219(5) Uani 1 1 d . . . . .
H00B H 0.884351 0.176644 0.854242 0.026 Uiso 1 1 calc R U . . .
C00C C 0.3345(3) 0.3269(4) 0.85355(15) 0.0169(4) Uani 1 1 d . . . . .
H00C H 0.348333 0.202461 0.815474 0.020 Uiso 1 1 calc R U . . .
C00D C 0.9156(3) 0.4688(5) 0.78943(16) 0.0226(5) Uani 1 1 d . . . . .
H00D H 1.025656 0.454722 0.781812 0.027 Uiso 1 1 calc R U . . .
C00E C 0.2503(3) 0.2995(4) 0.92590(15) 0.0190(4) Uani 1 1 d . . . . .
C00F C 0.2474(2) 0.6038(4) 0.59025(15) 0.0152(4) Uani 1 1 d . . . . .
C00G C 0.3855(2) 0.2091(6) 0.53878(13) 0.0188(4) Uani 1 1 d . . . . .
H00G H 0.430212 0.072439 0.520888 0.023 Uiso 1 1 calc R U . . .
C00H C 0.5897(3) 0.5083(4) 0.81110(14) 0.0157(4) Uani 1 1 d . . . . .
C00I C 0.8375(3) 0.6546(4) 0.75760(14) 0.0216(6) Uani 1 1 d . . . . .
H00I H 0.894558 0.768778 0.728638 0.026 Uiso 1 1 calc R U . . .
C00J C 0.1654(3) 0.2717(5) 0.99730(17) 0.0266(6) Uani 1 1 d . . . . .
C00K C 0.3903(2) 0.7198(6) 0.89784(13) 0.0188(4) Uani 1 1 d . . . . .
H00F H 0.440550 0.857294 0.878619 0.028 Uiso 1 1 calc R U . . .
H00H H 0.438034 0.669586 0.954486 0.028 Uiso 1 1 calc R U . . .
H00J H 0.278068 0.745568 0.906888 0.028 Uiso 1 1 calc R U . . .
C00L C 0.6756(2) 0.6742(5) 0.76798(14) 0.0183(6) Uani 1 1 d . . . . .
H00L H 0.623108 0.801383 0.745584 0.022 Uiso 1 1 calc R U . . .
H00A H 0.210(4) 0.230(8) 1.051(2) 0.038(9) Uiso 1 1 d . . . . .
H00E H 0.060(4) 0.299(6) 0.995(2) 0.030(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C005 1.899(2) . ?
N002 C003 1.387(3) . ?
N002 C00F 1.365(3) . ?
C003 C004 1.364(3) . ?
C004 C008 1.445(3) . ?
C004 C00A 1.525(3) . ?
C005 C006 1.378(3) . ?
C005 C00F 1.394(3) . ?
C006 C00G 1.407(3) . ?
C007 C008 1.404(3) . ?
C007 C00G 1.392(3) . ?
C008 C00F 1.413(3) . ?
C009 C00B 1.397(3) . ?
C009 C00H 1.391(3) . ?
C00A C00C 1.528(3) . ?
C00A C00H 1.539(3) . ?
C00A C00K 1.536(3) . ?
C00B C00D 1.385(4) . ?
C00C C00E 1.306(3) . ?
C00D C00I 1.390(3) . ?
C00E C00J 1.297(3) . ?
C00H C00L 1.401(4) . ?
C00I C00L 1.395(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
C00F N002 C003 108.47(19) . . ?
C004 C003 N002 110.1(2) . . ?
C003 C004 C008 106.61(19) . . ?
C003 C004 C00A 127.4(2) . . ?
C008 C004 C00A 125.9(2) . . ?
C006 C005 Br01 121.17(17) . . ?
C006 C005 C00F 119.5(2) . . ?
C00F C005 Br01 119.30(17) . . ?
C005 C006 C00G 120.3(2) . . ?
C00G C007 C008 119.4(2) . . ?
C007 C008 C004 134.6(2) . . ?
C007 C008 C00F 119.0(2) . . ?
C00F C008 C004 106.33(19) . . ?
C00H C009 C00B 120.8(2) . . ?
C004 C00A C00C 106.65(18) . . ?
C004 C00A C00H 109.44(17) . . ?
C004 C00A C00K 111.51(19) . . ?
C00C C00A C00H 110.62(18) . . ?
C00C C00A C00K 110.29(19) . . ?
C00K C00A C00H 108.34(17) . . ?
C00D C00B C009 120.4(2) . . ?
C00E C00C C00A 125.4(2) . . ?
C00B C00D C00I 119.4(2) . . ?
C00J C00E C00C 179.4(3) . . ?
N002 C00F C005 130.5(2) . . ?
N002 C00F C008 108.49(19) . . ?
C005 C00F C008 121.0(2) . . ?
C007 C00G C006 120.6(3) . . ?
C009 C00H C00A 122.7(2) . . ?
C009 C00H C00L 118.5(2) . . ?
C00L C00H C00A 118.7(2) . . ?
C00D C00I C00L 120.3(2) . . ?
C00I C00L C00H 120.6(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 1.241
_oxdiff_exptl_absorpt_empirical_full_min 0.881
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/CHCl3'
####################################################################### 
# 
# 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_SawanoKoba195b
_database_code_depnum_ccdc_archive 'CCDC 2382171'
loop_
_audit_author_name
_audit_author_address
'Eri Ishikawa'
;Chubu University
Japan
;
_audit_update_record             
;
2024-09-06 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H14 Br N'
_chemical_formula_moiety         'C18 H14 Br N'
_chemical_formula_weight         324.22
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.754(3)
_cell_length_b                   8.657(5)
_cell_length_c                   14.376(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.56(2)
_cell_angle_gamma                90.0000
_cell_volume                     713.8(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6723
_cell_measurement_theta_min      3.55
_cell_measurement_theta_max      27.48
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328.00
_exptl_absorpt_coefficient_mu    2.876
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.330
_exptl_absorpt_correction_T_max  0.422

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            7048
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_theta_max         27.463
_diffrn_reflns_theta_min         3.552
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3257
_reflns_number_gt                3046
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.985

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0703
_refine_ls_wR_factor_gt          0.0692
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         3257
_refine_ls_number_parameters     237
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0239P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1257 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(9)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.02077(6) 0.36835(6) 0.67046(2) 0.03661(13) Uani 1 1 d . . . . .
N1 N -0.0324(6) 0.3493(4) 0.44126(19) 0.0259(6) Uani 1 1 d . . . . .
C1 C 0.1831(7) 0.5821(4) 0.1779(2) 0.0248(7) Uani 1 1 d . . . . .
C2 C 0.3028(7) 0.7190(4) 0.1651(3) 0.0315(8) Uani 1 1 d . . . . .
C3 C 0.2003(8) 0.8361(4) 0.1090(3) 0.0383(9) Uani 1 1 d . . . . .
C4 C -0.0192(9) 0.8166(5) 0.0656(3) 0.0391(10) Uani 1 1 d . . . . .
C5 C -0.1426(7) 0.6816(5) 0.0779(3) 0.0358(9) Uani 1 1 d . . . . .
C6 C -0.0409(7) 0.5652(4) 0.1349(3) 0.0294(7) Uani 1 1 d . . . . .
C7 C 0.2973(6) 0.4532(4) 0.2373(2) 0.0235(7) Uani 1 1 d . . . . .
C8 C -0.0051(5) 0.3480(5) 0.3465(2) 0.0257(8) Uani 1 1 d . . . . .
C9 C 0.1889(6) 0.4315(4) 0.3287(2) 0.0227(6) Uani 1 1 d . . . . .
C10 C 0.2867(6) 0.4879(4) 0.4179(2) 0.0220(6) Uani 1 1 d . . . . .
C11 C 0.4852(7) 0.5757(4) 0.4460(3) 0.0263(8) Uani 1 1 d . . . . .
C12 C 0.5387(7) 0.6001(4) 0.5401(3) 0.0295(8) Uani 1 1 d . . . . .
C13 C 0.4029(7) 0.5396(4) 0.6074(3) 0.0280(7) Uani 1 1 d . . . . .
C14 C 0.2043(6) 0.4569(4) 0.5810(2) 0.0252(7) Uani 1 1 d . . . . .
C15 C 0.1443(6) 0.4324(4) 0.4858(2) 0.0226(6) Uani 1 1 d . . . . .
C16 C 0.2957(7) 0.3032(4) 0.1825(3) 0.0268(7) Uani 1 1 d . . . . .
C17 C 0.4796(7) 0.2340(4) 0.1555(2) 0.0267(7) Uani 1 1 d . . . . .
C18 C 0.6597(7) 0.1620(4) 0.1280(3) 0.0319(8) Uani 1 1 d . . . . .
H1 H 0.444(8) 0.732(4) 0.197(3) 0.025(10) Uiso 1 1 d . . . . .
H2 H 0.298(9) 0.928(6) 0.107(4) 0.057(16) Uiso 1 1 d . . . . .
H3 H -0.064(8) 0.891(7) 0.025(3) 0.043(13) Uiso 1 1 d . . . . .
H4 H -0.310(8) 0.663(5) 0.048(3) 0.034(11) Uiso 1 1 d . . . . .
H5 H -0.127(10) 0.479(7) 0.149(4) 0.057(15) Uiso 1 1 d . . . . .
H6 H 0.444(7) 0.478(4) 0.250(2) 0.011(8) Uiso 1 1 d . . . . .
H7 H -0.119(9) 0.287(5) 0.309(3) 0.039(12) Uiso 1 1 d . . . . .
H8 H 0.584(7) 0.617(4) 0.401(3) 0.017(9) Uiso 1 1 d . . . . .
H9 H 0.665(6) 0.661(4) 0.557(2) 0.012(8) Uiso 1 1 d . . . . .
H10 H 0.443(9) 0.558(5) 0.672(3) 0.039(11) Uiso 1 1 d . . . . .
H11 H -0.122(7) 0.314(4) 0.464(3) 0.017(10) Uiso 1 1 d . . . . .
H12 H 0.156(9) 0.256(5) 0.169(3) 0.038(12) Uiso 1 1 d . . . . .
H13 H 0.715(10) 0.176(6) 0.066(4) 0.062(15) Uiso 1 1 d . . . . .
H14 H 0.748(9) 0.090(5) 0.165(4) 0.044(13) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C14 1.890(4) . ?
N1 C15 1.363(5) . ?
N1 C8 1.384(4) . ?
N1 H11 0.70(4) . ?
C1 C2 1.390(5) . ?
C1 C6 1.392(5) . ?
C1 C7 1.521(5) . ?
C2 C3 1.397(6) . ?
C2 H1 0.91(4) . ?
C3 C4 1.374(7) . ?
C3 H2 0.98(5) . ?
C4 C5 1.386(6) . ?
C4 H3 0.90(5) . ?
C5 C6 1.397(5) . ?
C5 H4 1.03(4) . ?
C6 H5 0.93(6) . ?
C7 C9 1.511(5) . ?
C7 C16 1.518(5) . ?
C7 H6 0.87(4) . ?
C8 C9 1.371(5) . ?
C8 H7 0.97(5) . ?
C9 C10 1.444(4) . ?
C10 C11 1.404(5) . ?
C10 C15 1.408(5) . ?
C11 C12 1.379(5) . ?
C11 H8 0.97(4) . ?
C12 C13 1.394(6) . ?
C12 H9 0.91(4) . ?
C13 C14 1.376(5) . ?
C13 H10 0.95(5) . ?
C14 C15 1.402(4) . ?
C16 C17 1.301(6) . ?
C16 H12 0.91(5) . ?
C17 C18 1.298(6) . ?
C18 H13 0.98(6) . ?
C18 H14 0.94(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 N1 C8 109.1(3) . . ?
C15 N1 H11 124(3) . . ?
C8 N1 H11 127(3) . . ?
C2 C1 C6 118.7(3) . . ?
C2 C1 C7 120.2(3) . . ?
C6 C1 C7 121.0(3) . . ?
C1 C2 C3 120.3(4) . . ?
C1 C2 H1 118(2) . . ?
C3 C2 H1 121(2) . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H2 127(3) . . ?
C2 C3 H2 113(3) . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 H3 114(3) . . ?
C5 C4 H3 125(3) . . ?
C4 C5 C6 119.2(4) . . ?
C4 C5 H4 123(2) . . ?
C6 C5 H4 117(2) . . ?
C1 C6 C5 121.0(4) . . ?
C1 C6 H5 119(3) . . ?
C5 C6 H5 120(3) . . ?
C9 C7 C16 111.0(3) . . ?
C9 C7 C1 112.9(3) . . ?
C16 C7 C1 110.6(3) . . ?
C9 C7 H6 107(2) . . ?
C16 C7 H6 107(2) . . ?
C1 C7 H6 108(2) . . ?
C9 C8 N1 109.7(3) . . ?
C9 C8 H7 135(3) . . ?
N1 C8 H7 115(3) . . ?
C8 C9 C10 106.2(3) . . ?
C8 C9 C7 128.8(3) . . ?
C10 C9 C7 124.9(3) . . ?
C11 C10 C15 119.4(3) . . ?
C11 C10 C9 133.6(3) . . ?
C15 C10 C9 107.0(3) . . ?
C12 C11 C10 118.6(3) . . ?
C12 C11 H8 121(2) . . ?
C10 C11 H8 121(2) . . ?
C11 C12 C13 122.0(3) . . ?
C11 C12 H9 117(2) . . ?
C13 C12 H9 121(2) . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H10 119(3) . . ?
C12 C13 H10 121(3) . . ?
C13 C14 C15 118.9(3) . . ?
C13 C14 Br1 121.4(3) . . ?
C15 C14 Br1 119.7(3) . . ?
N1 C15 C14 130.9(3) . . ?
N1 C15 C10 108.0(3) . . ?
C14 C15 C10 120.9(3) . . ?
C17 C16 C7 125.2(3) . . ?
C17 C16 H12 117(3) . . ?
C7 C16 H12 118(3) . . ?
C18 C17 C16 178.5(4) . . ?
C17 C18 H13 123(3) . . ?
C17 C18 H14 124(3) . . ?
H13 C18 H14 113(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
C6 C1 C2 C3 -0.7(5) . . . . ?
C7 C1 C2 C3 178.6(3) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C2 C3 C4 C5 0.9(6) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C2 C1 C6 C5 1.5(5) . . . . ?
C7 C1 C6 C5 -177.9(4) . . . . ?
C4 C5 C6 C1 -1.0(6) . . . . ?
C2 C1 C7 C9 109.8(4) . . . . ?
C6 C1 C7 C9 -70.9(4) . . . . ?
C2 C1 C7 C16 -125.2(3) . . . . ?
C6 C1 C7 C16 54.2(4) . . . . ?
C15 N1 C8 C9 -0.5(4) . . . . ?
N1 C8 C9 C10 -0.1(4) . . . . ?
N1 C8 C9 C7 175.4(3) . . . . ?
C16 C7 C9 C8 -40.9(5) . . . . ?
C1 C7 C9 C8 84.0(4) . . . . ?
C16 C7 C9 C10 133.9(3) . . . . ?
C1 C7 C9 C10 -101.3(4) . . . . ?
C8 C9 C10 C11 178.2(4) . . . . ?
C7 C9 C10 C11 2.5(6) . . . . ?
C8 C9 C10 C15 0.7(4) . . . . ?
C7 C9 C10 C15 -175.0(3) . . . . ?
C15 C10 C11 C12 2.3(5) . . . . ?
C9 C10 C11 C12 -175.0(4) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
C11 C12 C13 C14 -2.2(6) . . . . ?
C12 C13 C14 C15 1.2(5) . . . . ?
C12 C13 C14 Br1 178.2(3) . . . . ?
C8 N1 C15 C14 -174.2(4) . . . . ?
C8 N1 C15 C10 0.9(4) . . . . ?
C13 C14 C15 N1 176.1(4) . . . . ?
Br1 C14 C15 N1 -1.0(5) . . . . ?
C13 C14 C15 C10 1.5(5) . . . . ?
Br1 C14 C15 C10 -175.6(2) . . . . ?
C11 C10 C15 N1 -178.9(3) . . . . ?
C9 C10 C15 N1 -1.0(4) . . . . ?
C11 C10 C15 C14 -3.2(5) . . . . ?
C9 C10 C15 C14 174.7(3) . . . . ?
C9 C7 C16 C17 -121.4(4) . . . . ?
C1 C7 C16 C17 112.5(4) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
7-Bromo-3-(1-phenylbuta-2,3-dien-1-yl)-1H-indole
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/CHCl3'
