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

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

data_lfy_100k_32
_database_code_depnum_ccdc_archive 'CCDC 2085362'
loop_
_audit_author_name
_audit_author_address
'Jun Xu'
;Tianjin University, School of Pharmaceutical Science and Technology
China
;
_audit_update_record             
;
2021-05-24 deposited with the CCDC.	2021-05-26 downloaded from the CCDC.
;
_audit_creation_date             2021-05-24
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
'Ethyl 6-bromo-4,7-dimethyl-2-phenyl-1H-indole-3-carboxylate'
_chemical_formula_moiety         'C19 H18 Br N O2'
_chemical_formula_sum            'C19 H18 Br N O2'
_chemical_formula_weight         372.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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      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                   12.1783(2)
_cell_length_b                   7.56305(18)
_cell_length_c                   17.6627(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.5451(16)
_cell_angle_gamma                90
_cell_volume                     1626.75(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3677
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      76.0030
_cell_measurement_theta_min      3.6050
_shelx_estimated_absorpt_T_max   0.902
_shelx_estimated_absorpt_T_min   0.844
_exptl_absorpt_coefficient_mu    3.516
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9497
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.360
_diffrn_reflns_theta_min         3.630
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      159.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.946
_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  22.00   0.50    2.28    --  -47.00  24.00  52.00  142
  2  ω     34.00 121.00   0.50    2.28    --   47.00  24.00  52.00  174
  3  ω    106.00 177.00   0.50    9.10    --  107.61  24.00  52.00  142
  4  ω     93.00 178.00   0.50    9.10    --  107.61  19.00 120.00  170
  5  ω     74.00 122.00   0.50    9.10    --  107.61 -24.00-111.00   96
  6  ω     64.00 106.00   0.50    9.10    --  107.61 -99.00   0.00   84
  7  ω     46.00  85.00   0.50    9.10    --  107.61 -99.00  30.00   78
  8  ω     36.00 108.00   0.50    9.10    --  107.61 -99.00-120.00  144
  9  ω     -7.00  18.00   0.50    2.28    --   47.00 -24.00-111.00   50
 10  ω    -89.00 -35.00   0.50    2.28    --  -47.00 125.00 120.00  108
 11  ω   -101.00 -27.00   0.50    9.10    -- -100.00 125.00 150.00  148
 12  ω    -80.00 -54.00   0.50    9.10    -- -100.00  24.00  52.00   52
 13  ω   -117.00 -33.00   0.50    2.28    --  -47.00 -24.00-111.00  168
 14  ω   -131.00 -86.00   0.50    9.10    -- -100.00 -24.00-111.00   90
 15  ω    -61.00 -33.00   0.50    9.10    -- -100.00 125.00 -90.00   56
 16  ω    -99.00 -73.00   0.50    9.10    -- -100.00 125.00 -90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0738818000
_diffrn_orient_matrix_UB_12      -0.0567663000
_diffrn_orient_matrix_UB_13      0.0660268000
_diffrn_orient_matrix_UB_21      0.0956473000
_diffrn_orient_matrix_UB_22      0.0317398000
_diffrn_orient_matrix_UB_23      0.0560680000
_diffrn_orient_matrix_UB_31      -0.0373388000
_diffrn_orient_matrix_UB_32      0.1930829000
_diffrn_orient_matrix_UB_33      0.0101459000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2463
_reflns_number_total             3234
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (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         1.019
_refine_diff_density_min         -1.297
_refine_diff_density_rms         0.146
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.098
_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)+(0.1273P)²+0.4850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.1987
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C6(H6), C12(H12), C14(H14), C16(H16)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), 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
Br1 Br 0.82257(4) 0.65001(8) 0.56285(3) 0.0403(2) Uani 1 1 d . . . . .
O1 O 0.6342(2) 0.2960(5) 0.13069(18) 0.0337(8) Uani 1 1 d . . . . .
O2 O 0.7946(2) 0.4253(5) 0.15760(18) 0.0314(7) Uani 1 1 d . . . . .
N1 N 0.5415(3) 0.5610(6) 0.33369(19) 0.0268(8) Uani 1 1 d . . . . .
H1 H 0.482134 0.598408 0.354208 0.032 Uiso 1 1 calc R . . . .
C1 C 0.3539(4) 0.5877(8) 0.0989(3) 0.0353(11) Uani 1 1 d . . . . .
H1A H 0.354902 0.637653 0.050855 0.042 Uiso 1 1 calc R . . . .
C2 C 0.2556(4) 0.4471(8) 0.1987(3) 0.0367(11) Uani 1 1 d . . . . .
H2 H 0.190434 0.401152 0.217432 0.044 Uiso 1 1 calc R . . . .
C3 C 0.6666(4) 0.6071(7) 0.4429(3) 0.0298(10) Uani 1 1 d . . . . .
C4 C 0.6564(3) 0.4506(7) 0.2481(2) 0.0279(9) Uani 1 1 d . . . . .
C5 C 0.4487(3) 0.5039(7) 0.2137(2) 0.0292(10) Uani 1 1 d . . . . .
C6 C 0.4494(4) 0.5785(7) 0.1421(3) 0.0318(10) Uani 1 1 d . . . . .
H6 H 0.514578 0.622892 0.122716 0.038 Uiso 1 1 calc R . . . .
C7 C 0.6909(3) 0.3811(6) 0.1741(3) 0.0275(9) Uani 1 1 d . . . . .
C8 C 0.9161(4) 0.3655(8) 0.2969(3) 0.0401(13) Uani 1 1 d . . . . .
H8A H 0.886103 0.263581 0.271779 0.060 Uiso 1 1 calc GR . . . .
H8B H 0.975729 0.329810 0.329419 0.060 Uiso 1 1 calc GR . . . .
H8C H 0.942534 0.447663 0.259867 0.060 Uiso 1 1 calc GR . . . .
C9 C 0.5832(4) 0.6898(8) 0.4937(3) 0.0350(11) Uani 1 1 d . . . . .
H9A H 0.604759 0.809027 0.505169 0.052 Uiso 1 1 calc GR . . . .
H9B H 0.578684 0.622995 0.539771 0.052 Uiso 1 1 calc GR . . . .
H9C H 0.512871 0.690408 0.468731 0.052 Uiso 1 1 calc GR . . . .
C10 C 0.8357(4) 0.3591(8) 0.0866(3) 0.0380(12) Uani 1 1 d . . . . .
H10A H 0.804839 0.426202 0.044743 0.046 Uiso 1 1 calc R . . . .
H10B H 0.815501 0.235895 0.080181 0.046 Uiso 1 1 calc R . . . .
C11 C 0.5494(3) 0.5005(6) 0.2618(2) 0.0256(9) Uani 1 1 d . . . . .
C12 C 0.2568(4) 0.5217(8) 0.1281(3) 0.0373(11) Uani 1 1 d . . . . .
H12 H 0.192328 0.528083 0.099580 0.045 Uiso 1 1 calc R . . . .
C13 C 0.7191(3) 0.4820(6) 0.3170(2) 0.0257(9) Uani 1 1 d . . . . .
C14 C 0.8527(4) 0.4990(7) 0.4166(3) 0.0332(10) Uani 1 1 d . . . . .
H14 H 0.922913 0.477615 0.435569 0.040 Uiso 1 1 calc R . . . .
C15 C 0.6436(3) 0.5538(7) 0.3694(2) 0.0286(10) Uani 1 1 d . . . . .
C16 C 0.3509(4) 0.4391(7) 0.2428(3) 0.0333(10) Uani 1 1 d . . . . .
H16 H 0.349107 0.391014 0.291260 0.040 Uiso 1 1 calc R . . . .
C17 C 0.8285(3) 0.4522(7) 0.3433(3) 0.0326(10) Uani 1 1 d . . . . .
C18 C 0.7753(4) 0.5778(7) 0.4639(2) 0.0317(10) Uani 1 1 d . . . . .
C19 C 0.9586(4) 0.3780(10) 0.0885(4) 0.0506(15) Uani 1 1 d . . . . .
H19A H 0.987780 0.345763 0.040095 0.076 Uiso 1 1 calc GR . . . .
H19B H 0.988829 0.301859 0.126842 0.076 Uiso 1 1 calc GR . . . .
H19C H 0.977647 0.498415 0.099664 0.076 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
Br1 C18 1.915(4) . ?
O1 C7 1.211(6) . ?
O2 C7 1.342(5) . ?
O2 C10 1.444(6) . ?
N1 H1 0.8600 . ?
N1 C11 1.353(6) . ?
N1 C15 1.389(5) . ?
C1 H1A 0.9300 . ?
C1 C6 1.386(6) . ?
C1 C12 1.387(7) . ?
C2 H2 0.9300 . ?
C2 C12 1.369(8) . ?
C2 C16 1.393(6) . ?
C3 C9 1.498(7) . ?
C3 C15 1.384(6) . ?
C3 C18 1.389(6) . ?
C4 C7 1.473(6) . ?
C4 C11 1.380(6) . ?
C4 C13 1.452(6) . ?
C5 C6 1.386(7) . ?
C5 C11 1.486(6) . ?
C5 C16 1.391(7) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 C17 1.502(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C19 1.503(7) . ?
C12 H12 0.9300 . ?
C13 C15 1.419(6) . ?
C13 C17 1.425(6) . ?
C14 H14 0.9300 . ?
C14 C17 1.372(7) . ?
C14 C18 1.398(7) . ?
C16 H16 0.9300 . ?
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
C7 O2 C10 115.9(4) . . ?
C11 N1 H1 125.0 . . ?
C11 N1 C15 110.0(4) . . ?
C15 N1 H1 125.0 . . ?
C6 C1 H1A 120.3 . . ?
C6 C1 C12 119.5(5) . . ?
C12 C1 H1A 120.3 . . ?
C12 C2 H2 119.6 . . ?
C12 C2 C16 120.8(4) . . ?
C16 C2 H2 119.6 . . ?
C15 C3 C9 123.4(4) . . ?
C15 C3 C18 112.8(4) . . ?
C18 C3 C9 123.8(4) . . ?
C11 C4 C7 122.1(4) . . ?
C11 C4 C13 107.3(4) . . ?
C13 C4 C7 130.6(4) . . ?
C6 C5 C11 121.2(4) . . ?
C6 C5 C16 119.6(4) . . ?
C16 C5 C11 119.2(4) . . ?
C1 C6 C5 120.6(4) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O1 C7 O2 121.8(4) . . ?
O1 C7 C4 125.8(4) . . ?
O2 C7 C4 112.4(4) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C17 C8 H8A 109.5 . . ?
C17 C8 H8B 109.5 . . ?
C17 C8 H8C 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 H10A 110.2 . . ?
O2 C10 H10B 110.2 . . ?
O2 C10 C19 107.5(4) . . ?
H10A C10 H10B 108.5 . . ?
C19 C10 H10A 110.2 . . ?
C19 C10 H10B 110.2 . . ?
N1 C11 C4 109.5(3) . . ?
N1 C11 C5 117.7(4) . . ?
C4 C11 C5 132.8(4) . . ?
C1 C12 H12 119.9 . . ?
C2 C12 C1 120.2(4) . . ?
C2 C12 H12 119.9 . . ?
C15 C13 C4 105.7(3) . . ?
C15 C13 C17 117.3(4) . . ?
C17 C13 C4 136.9(4) . . ?
C17 C14 H14 118.9 . . ?
C17 C14 C18 122.3(4) . . ?
C18 C14 H14 118.9 . . ?
N1 C15 C13 107.5(4) . . ?
C3 C15 N1 125.9(4) . . ?
C3 C15 C13 126.6(4) . . ?
C2 C16 H16 120.3 . . ?
C5 C16 C2 119.3(5) . . ?
C5 C16 H16 120.3 . . ?
C13 C17 C8 124.0(4) . . ?
C14 C17 C8 118.8(4) . . ?
C14 C17 C13 117.2(4) . . ?
C3 C18 Br1 118.4(4) . . ?
C3 C18 C14 123.7(4) . . ?
C14 C18 Br1 117.9(3) . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_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 3.395
_oxdiff_exptl_absorpt_empirical_full_min 0.467
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
