#------------------------------------------------------------------------------
#$Date: 2021-07-05 21:10:35 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267228 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158099.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158099
loop_
_publ_author_name
'Zhao, Lan'
'Qiu, Changfu'
'Zhao, Lixin'
'Yin, Guangwei'
'Li, Fangyi'
'Wang, Chunhua'
'Li, Zheng'
_publ_section_title
;
Base-promoted, CBr4-mediated tandem bromination/intramolecular
Friedel-Crafts alkylation of N-aryl enamines: a facile access to 1H- and
3H-indoles.
;
_journal_issue 24
_journal_name_full 'Organic & biomolecular chemistry'
_journal_page_first 5377
_journal_page_last 5382
_journal_paper_doi 10.1039/d1ob00731a
_journal_volume 19
_journal_year 2021
_chemical_formula_moiety 'C19 H18 Br N O2'
_chemical_formula_sum 'C19 H18 Br N O2'
_chemical_formula_weight 372.25
_chemical_name_systematic
'Ethyl 6-bromo-4,7-dimethyl-2-phenyl-1H-indole-3-carboxylate'
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_Hall '-P 2ybc'
_space_group_name_H-M_alt 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_audit_creation_date 2021-05-24
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-05-24 deposited with the CCDC. 2021-05-26 downloaded from the CCDC.
;
_cell_angle_alpha 90
_cell_angle_beta 90.5451(16)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 12.1783(2)
_cell_length_b 7.56305(18)
_cell_length_c 17.6627(3)
_cell_measurement_reflns_used 3677
_cell_measurement_temperature 159.99(10)
_cell_measurement_theta_max 76.0030
_cell_measurement_theta_min 3.6050
_cell_volume 1626.75(5)
_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)'
_diffrn_ambient_environment N~2~
_diffrn_ambient_temperature 159.99(10)
_diffrn_detector 'CCD plate'
_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 t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -49.00 22.00 0.50 2.28 -- -47.00 24.00 52.00 142
2 \w 34.00 121.00 0.50 2.28 -- 47.00 24.00 52.00 174
3 \w 106.00 177.00 0.50 9.10 -- 107.61 24.00 52.00 142
4 \w 93.00 178.00 0.50 9.10 -- 107.61 19.00 120.00 170
5 \w 74.00 122.00 0.50 9.10 -- 107.61 -24.00-111.00 96
6 \w 64.00 106.00 0.50 9.10 -- 107.61 -99.00 0.00 84
7 \w 46.00 85.00 0.50 9.10 -- 107.61 -99.00 30.00 78
8 \w 36.00 108.00 0.50 9.10 -- 107.61 -99.00-120.00 144
9 \w -7.00 18.00 0.50 2.28 -- 47.00 -24.00-111.00 50
10 \w -89.00 -35.00 0.50 2.28 -- -47.00 125.00 120.00 108
11 \w -101.00 -27.00 0.50 9.10 -- -100.00 125.00 150.00 148
12 \w -80.00 -54.00 0.50 9.10 -- -100.00 24.00 52.00 52
13 \w -117.00 -33.00 0.50 2.28 -- -47.00 -24.00-111.00 168
14 \w -131.00 -86.00 0.50 9.10 -- -100.00 -24.00-111.00 90
15 \w -61.00 -33.00 0.50 9.10 -- -100.00 125.00 -90.00 56
16 \w -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 '\w 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_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_source 'Rotating-anode X-ray tube'
_diffrn_source_type 'Rigaku (Cu) X-ray Source'
_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_crystal_colour 'clear light colourless'
_exptl_crystal_density_diffrn 1.520
_exptl_crystal_description block
_exptl_crystal_F_000 760
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max 0.05
_exptl_crystal_size_mid 0.03
_exptl_crystal_size_min 0.03
_refine_diff_density_max 1.019
_refine_diff_density_min -1.297
_refine_diff_density_rms 0.146
_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_restrained_S_all 1.098
_refine_ls_R_factor_all 0.0847
_refine_ls_R_factor_gt 0.0641
_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/[\s^2^(Fo^2^)+(0.1273P)^2^+0.4850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1701
_refine_ls_wR_factor_ref 0.1987
_reflns_Friedel_coverage 0.000
_reflns_number_gt 2463
_reflns_number_total 3234
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file d1ob00731a2.cif
_cod_data_source_block lfy_100k_32
_cod_depositor_comments 'Adding full bibliography for 7158099.cif.'
_cod_original_cell_volume 1626.75(6)
_cod_database_code 7158099
_shelx_shelxl_version_number 2018/1
_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.
;
_shelx_estimated_absorpt_t_max 0.902
_shelx_estimated_absorpt_t_min 0.844
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.49
_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)
;
_shelx_res_file
;
TITL lfy_100k_32_a.res in P2(1)/c
lfy_100k_32.res
created by SHELXL-2018/1 at 08:34:50 on 24-May-2021
REM Old TITL LFY_100K_32 in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.134, Rweak 0.003, Alpha 0.057, Orientation as input
REM Formula found by SHELXT: C19 N O2 Br
CELL 1.54184 12.17832 7.563052 17.662663 90 90.5451 90
ZERR 4 0.00021 0.000179 0.000334 0 0.0016 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Br N O
UNIT 76 72 4 4 8
L.S. 10
PLAN 20
SIZE 0.03 0.03 0.05
BOND $H
LIST 4
fmap 2
acta
OMIT -10 5 8
OMIT -6 8 3
REM
REM
REM
WGHT 0.127300 0.485000
FVAR 1.19976
BR1 3 0.822572 0.650011 0.562852 11.00000 0.03991 0.04997 =
0.03094 -0.00476 -0.01017 -0.00325
O1 5 0.634221 0.296016 0.130694 11.00000 0.02527 0.04595 =
0.02981 -0.00720 -0.00027 -0.00753
O2 5 0.794636 0.425336 0.157604 11.00000 0.02145 0.04204 =
0.03071 -0.00547 -0.00015 -0.00166
N1 4 0.541535 0.561014 0.333691 11.00000 0.02006 0.03838 =
0.02208 -0.00017 -0.00163 0.00121
AFIX 43
H1 2 0.482134 0.598408 0.354208 11.00000 -1.20000
AFIX 0
C1 1 0.353898 0.587653 0.098948 11.00000 0.03185 0.04352 =
0.03025 -0.00121 -0.00980 0.00729
AFIX 43
H1A 2 0.354902 0.637653 0.050855 11.00000 -1.20000
AFIX 0
C2 1 0.255613 0.447051 0.198711 11.00000 0.01964 0.04559 =
0.04476 -0.00649 -0.00123 -0.00159
AFIX 43
H2 2 0.190434 0.401152 0.217432 11.00000 -1.20000
AFIX 0
C3 1 0.666561 0.607147 0.442852 11.00000 0.03159 0.02841 =
0.02943 0.00475 -0.00246 -0.00264
C4 1 0.656357 0.450645 0.248063 11.00000 0.02107 0.03493 =
0.02765 -0.00163 -0.00199 -0.00015
C5 1 0.448675 0.503876 0.213693 11.00000 0.02395 0.03626 =
0.02730 -0.00285 -0.00327 0.00518
C6 1 0.449382 0.578508 0.142053 11.00000 0.02517 0.03745 =
0.03266 0.00158 -0.00396 0.00160
AFIX 43
H6 2 0.514578 0.622892 0.122716 11.00000 -1.20000
AFIX 0
C7 1 0.690851 0.381107 0.174108 11.00000 0.02194 0.02922 =
0.03126 0.00156 -0.00358 -0.00017
C8 1 0.916126 0.365492 0.296904 11.00000 0.02369 0.06021 =
0.03616 -0.00067 -0.00655 0.00718
AFIX 137
H8A 2 0.886103 0.263581 0.271779 11.00000 -1.50000
H8B 2 0.975729 0.329810 0.329419 11.00000 -1.50000
H8C 2 0.942534 0.447663 0.259867 11.00000 -1.50000
AFIX 0
C9 1 0.583236 0.689819 0.493697 11.00000 0.03565 0.04116 =
0.02805 -0.00232 -0.00217 -0.00005
AFIX 137
H9A 2 0.604759 0.809027 0.505169 11.00000 -1.50000
H9B 2 0.578684 0.622995 0.539771 11.00000 -1.50000
H9C 2 0.512871 0.690408 0.468731 11.00000 -1.50000
AFIX 0
C10 1 0.835716 0.359075 0.086618 11.00000 0.03410 0.04577 =
0.03412 -0.01058 0.00452 -0.00059
AFIX 23
H10A 2 0.804839 0.426202 0.044743 11.00000 -1.20000
H10B 2 0.815501 0.235895 0.080181 11.00000 -1.20000
AFIX 0
C11 1 0.549401 0.500523 0.261848 11.00000 0.02197 0.02821 =
0.02644 0.00131 -0.00446 -0.00304
C12 1 0.256802 0.521651 0.128088 11.00000 0.02691 0.04560 =
0.03917 -0.00674 -0.01095 0.00131
AFIX 43
H12 2 0.192328 0.528083 0.099580 11.00000 -1.20000
AFIX 0
C13 1 0.719128 0.482044 0.317031 11.00000 0.01966 0.02756 =
0.02992 0.00177 -0.00394 -0.00019
C14 1 0.852650 0.499012 0.416624 11.00000 0.02420 0.03913 =
0.03600 -0.00036 -0.00621 0.00041
AFIX 43
H14 2 0.922913 0.477615 0.435569 11.00000 -1.20000
AFIX 0
C15 1 0.643571 0.553811 0.369432 11.00000 0.02436 0.03239 =
0.02893 0.00549 -0.00402 0.00085
C16 1 0.350864 0.439110 0.242828 11.00000 0.02419 0.03996 =
0.03585 -0.00081 -0.00085 0.00212
AFIX 43
H16 2 0.349107 0.391014 0.291260 11.00000 -1.20000
AFIX 0
C17 1 0.828550 0.452180 0.343278 11.00000 0.02115 0.03948 =
0.03706 0.00499 -0.00643 0.00333
C18 1 0.775266 0.577764 0.463858 11.00000 0.03269 0.04087 =
0.02143 -0.00089 -0.00513 -0.00360
C19 1 0.958596 0.377987 0.088472 11.00000 0.02836 0.07494 =
0.04870 -0.00066 0.00682 0.00727
AFIX 137
H19A 2 0.987780 0.345763 0.040095 11.00000 -1.50000
H19B 2 0.988829 0.301859 0.126842 11.00000 -1.50000
H19C 2 0.977647 0.498415 0.099664 11.00000 -1.50000
AFIX 0
HKLF 4
REM lfy_100k_32_a.res in P2(1)/c
REM R1 = 0.0641 for 2463 Fo > 4sig(Fo) and 0.0847 for all 3234 data
REM 211 parameters refined using 0 restraints
END
WGHT 0.1274 0.4819
REM Highest difference peak 1.019, deepest hole -1.297, 1-sigma level 0.146
Q1 1 0.7464 0.6588 0.5844 11.00000 0.05 1.02
Q2 1 0.8852 0.6527 0.5389 11.00000 0.05 0.86
Q3 1 0.8123 0.5373 0.5629 11.00000 0.05 0.79
Q4 1 0.7979 0.7705 0.5609 11.00000 0.05 0.76
Q5 1 0.7578 0.6619 0.5165 11.00000 0.05 0.69
Q6 1 0.9056 0.6454 0.6045 11.00000 0.05 0.67
Q7 1 0.8235 0.0918 0.1059 11.00000 0.05 0.65
Q8 1 0.8503 0.7816 0.5628 11.00000 0.05 0.63
Q9 1 0.8158 0.6016 0.1038 11.00000 0.05 0.61
Q10 1 0.8233 0.6033 0.0220 11.00000 0.05 0.59
Q11 1 0.8240 0.0899 0.0217 11.00000 0.05 0.58
Q12 1 0.7763 0.5974 0.5009 11.00000 0.05 0.54
Q13 1 0.7115 0.5708 0.4646 11.00000 0.05 0.54
Q14 1 0.7816 0.4965 0.3394 11.00000 0.05 0.50
Q15 1 0.6752 0.4359 0.2207 11.00000 0.05 0.45
Q16 1 0.8743 0.6618 0.1607 11.00000 0.05 0.44
Q17 1 0.6803 0.3419 0.0606 11.00000 0.05 0.44
Q18 1 0.5137 0.4753 0.2352 11.00000 0.05 0.43
Q19 1 0.7036 0.4646 0.2741 11.00000 0.05 0.43
Q20 1 0.5936 0.5320 0.3613 11.00000 0.05 0.42
;
_shelx_res_checksum 88423
_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
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'
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 . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0399(4) 0.0500(4) 0.0309(3) -0.0048(2) -0.0102(2) -0.0032(2)
O1 0.0253(14) 0.046(2) 0.0298(16) -0.0072(14) -0.0003(12) -0.0075(14)
O2 0.0214(14) 0.042(2) 0.0307(15) -0.0055(14) -0.0001(11) -0.0017(14)
N1 0.0201(16) 0.038(2) 0.0221(16) -0.0002(15) -0.0016(12) 0.0012(15)
C1 0.032(2) 0.044(3) 0.030(2) -0.001(2) -0.0098(18) 0.007(2)
C2 0.020(2) 0.046(3) 0.045(3) -0.006(2) -0.0012(18) -0.002(2)
C3 0.032(2) 0.028(3) 0.029(2) 0.0048(18) -0.0025(18) -0.0026(18)
C4 0.0211(19) 0.035(3) 0.028(2) -0.0016(18) -0.0020(15) -0.0002(18)
C5 0.0239(19) 0.036(3) 0.027(2) -0.0029(18) -0.0033(16) 0.0052(18)
C6 0.025(2) 0.037(3) 0.033(2) 0.002(2) -0.0040(16) 0.0016(19)
C7 0.0219(19) 0.029(3) 0.031(2) 0.0016(18) -0.0036(16) -0.0002(17)
C8 0.024(2) 0.060(4) 0.036(3) -0.001(2) -0.0065(18) 0.007(2)
C9 0.036(2) 0.041(3) 0.028(2) -0.002(2) -0.0022(18) 0.000(2)
C10 0.034(2) 0.046(3) 0.034(3) -0.011(2) 0.0045(19) -0.001(2)
C11 0.0220(19) 0.028(3) 0.026(2) 0.0013(17) -0.0045(15) -0.0030(16)
C12 0.027(2) 0.046(3) 0.039(3) -0.007(2) -0.0109(18) 0.001(2)
C13 0.0197(18) 0.028(2) 0.030(2) 0.0018(17) -0.0039(15) -0.0002(17)
C14 0.024(2) 0.039(3) 0.036(2) 0.000(2) -0.0062(17) 0.0004(19)
C15 0.024(2) 0.032(3) 0.029(2) 0.0055(18) -0.0040(16) 0.0008(18)
C16 0.024(2) 0.040(3) 0.036(2) -0.001(2) -0.0009(17) 0.002(2)
C17 0.0212(19) 0.039(3) 0.037(2) 0.005(2) -0.0064(17) 0.0033(18)
C18 0.033(2) 0.041(3) 0.0214(19) -0.0009(19) -0.0051(16) -0.004(2)
C19 0.028(2) 0.075(5) 0.049(3) -0.001(3) 0.007(2) 0.007(3)
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'
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 . . ?
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 . ?