#------------------------------------------------------------------------------
#$Date: 2016-02-14 14:26:36 +0000 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238990.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_2238990
loop_
_publ_author_name
'Lai, Hongshan'
'Gallucci, Judith C.'
'Li, Chenglong'
_publ_section_title
;
(E)-3-(9-Ethyl-9H-carbazol-3-yl)-1-(2-methoxyphenyl)prop-2-en-1-one
;
_journal_coeditor_code LH5681
_journal_issue 2
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o190
_journal_paper_doi 10.1107/S1600536814001263
_journal_volume 70
_journal_year 2014
_chemical_formula_iupac 'C24 H21 N1 O2'
_chemical_formula_moiety 'C24 H21 N1 O2'
_chemical_formula_sum 'C24 H21 N O2'
_chemical_formula_weight 355.42
_chemical_name_systematic
(E)-3-(9-Ethyl-9H-carbazol-3-yl)-1-(2-methoxyphenyl)prop-2-en-1-one
_space_group_IT_number 61
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_Hall '-P 2ac 2ab'
_symmetry_space_group_name_H-M 'P b c a'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method 'WinGX routine CIF_UPDATE'
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_formula_units_Z 8
_cell_length_a 15.9332(7)
_cell_length_b 7.8915(3)
_cell_length_c 30.4062(14)
_cell_measurement_reflns_used 3814
_cell_measurement_temperature 150(2)
_cell_measurement_theta_max 25.03
_cell_measurement_theta_min 1.02
_cell_volume 3823.2(3)
_computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection 'COLLECT (Bruker, 2008)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON
(Spek, 2009)
;
_computing_publication_material 'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature 150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type 'Nonius KappaCCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'horizonally mounted graphite crystal'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.070
_diffrn_reflns_limit_h_max 18
_diffrn_reflns_limit_h_min -18
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 35
_diffrn_reflns_limit_l_min -36
_diffrn_reflns_number 31757
_diffrn_reflns_theta_full 25
_diffrn_reflns_theta_max 24.999
_diffrn_reflns_theta_min 1.339
_exptl_absorpt_coefficient_mu 0.078
_exptl_absorpt_correction_T_max 0.998
_exptl_absorpt_correction_T_min 0.746
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(HKL Scalepack; Otwinowski & Minor, 1997)'
_exptl_crystal_colour 'pale yellow'
_exptl_crystal_density_diffrn 1.235
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description 'rectangular plate'
_exptl_crystal_F_000 1504
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.27
_exptl_crystal_size_min 0.02
_refine_diff_density_max 0.164
_refine_diff_density_min -0.14
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.001
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_constraints 0
_refine_ls_number_parameters 246
_refine_ls_number_reflns 3352
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.001
_refine_ls_R_factor_all 0.1193
_refine_ls_R_factor_gt 0.0475
_refine_ls_shift/su_max 0
_refine_ls_shift/su_mean 0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0412P)^2^+0.2950P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.083
_refine_ls_wR_factor_ref 0.1016
_reflns_number_gt 1845
_reflns_number_total 3352
_reflns_threshold_expression 'I > 2\s(I)'
_iucr_refine_instructions_details
;
TITL HLCL-66 in Pbca
CELL 0.71073 15.9332 7.8915 30.4062 90.000 90.000 90.000
ZERR 8.00 0.0007 0.0003 0.0014 0.000 0.000 0.000
LATT 1
SYMM 1/2 - X, - Y, 1/2 + Z
SYMM 1/2 + X, 1/2 - Y, - Z
SYMM - X, 1/2 + Y, 1/2 - Z
SFAC C H N O
UNIT 192 168 8 16
ACTA 50.0
MERG 2
FMAP 2
PLAN -25
TEMP -123
BOND
BOND $H
CONF
MPLA 13 C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 N
MPLA 6 C18 C19 C20 C21 C22 C23
MPLA 13 C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 N
MPLA 4 C15 C16 C17 O1
EQIV $1 x-1/2, y, -z+1/2
HTAB C2 O1_$1
HTAB C13 O1_$1
EQIV $2 -x+3/2, y-1/2, z
HTAB C16 O1_$2
HTAB C24 O1_$2
L.S. 4
WGHT 0.041200 0.295000
FVAR 0.17954
C1 1 0.581074 0.417981 0.168647 11.00000 0.03455 0.03919 =
0.03586 0.00015 0.00546 0.00072
C2 1 0.559716 0.481251 0.127274 11.00000 0.04044 0.05002 =
0.03713 -0.00380 0.00105 -0.00001
AFIX 43
H2 2 0.513676 0.436340 0.111203 11.00000 -1.20000
AFIX 0
C3 1 0.607918 0.611387 0.110581 11.00000 0.05353 0.05430 =
0.03517 0.00490 0.00089 0.00370
AFIX 43
H3 2 0.594340 0.657367 0.082597 11.00000 -1.20000
AFIX 0
C4 1 0.676420 0.677531 0.133850 11.00000 0.05437 0.04847 =
0.04470 0.00642 0.00433 -0.00758
AFIX 43
H4 2 0.708882 0.766340 0.121378 11.00000 -1.20000
AFIX 0
C5 1 0.696961 0.614416 0.174747 11.00000 0.04249 0.04993 =
0.04297 0.00113 -0.00236 -0.00747
AFIX 43
H5 2 0.743313 0.659401 0.190556 11.00000 -1.20000
AFIX 0
C6 1 0.648964 0.483954 0.192608 11.00000 0.03289 0.03595 =
0.03461 -0.00204 0.00211 -0.00005
C7 1 0.650092 0.395568 0.234045 11.00000 0.03351 0.03409 =
0.03402 -0.00090 0.00096 0.00046
C8 1 0.701277 0.403805 0.271007 11.00000 0.03143 0.03580 =
0.04131 -0.00064 0.00222 -0.00221
AFIX 43
H8 2 0.747540 0.479732 0.271389 11.00000 -1.20000
AFIX 0
C9 1 0.685454 0.301857 0.307519 11.00000 0.03322 0.03538 =
0.03787 -0.00021 0.00052 0.00155
C10 1 0.616724 0.188997 0.305915 11.00000 0.03803 0.04389 =
0.03930 0.00481 0.00199 -0.00029
AFIX 43
H10 2 0.605103 0.120261 0.330831 11.00000 -1.20000
AFIX 0
C11 1 0.566150 0.175373 0.269519 11.00000 0.03443 0.04171 =
0.04672 0.00408 0.00109 -0.00830
AFIX 43
H11 2 0.520665 0.097561 0.269017 11.00000 -1.20000
AFIX 0
C12 1 0.583097 0.278584 0.233216 11.00000 0.03164 0.03811 =
0.03529 -0.00042 0.00172 0.00151
C13 1 0.474189 0.183169 0.177627 11.00000 0.04379 0.06230 =
0.04364 0.00419 -0.00594 -0.01720
AFIX 23
H13A 2 0.433147 0.252387 0.161048 11.00000 -1.20000
H13B 2 0.444726 0.133373 0.203214 11.00000 -1.20000
AFIX 0
C14 1 0.505501 0.042358 0.148495 11.00000 0.09780 0.06340 =
0.08718 -0.01949 0.00535 -0.02339
AFIX 137
H14A 2 0.536476 0.090687 0.123635 11.00000 -1.50000
H14B 2 0.457695 -0.023243 0.137477 11.00000 -1.50000
H14C 2 0.542706 -0.031994 0.165416 11.00000 -1.50000
AFIX 0
C15 1 0.741852 0.315173 0.344850 11.00000 0.03384 0.03777 =
0.03992 0.00021 0.00026 -0.00114
AFIX 43
H15 2 0.786722 0.393257 0.341298 11.00000 -1.20000
AFIX 0
C16 1 0.740251 0.234060 0.383569 11.00000 0.03253 0.04180 =
0.03923 -0.00017 0.00150 -0.00345
AFIX 43
H16 2 0.695989 0.157315 0.390010 11.00000 -1.20000
AFIX 0
C17 1 0.806889 0.263753 0.416050 11.00000 0.03329 0.03841 =
0.03906 -0.00338 0.00420 0.00145
C18 1 0.805720 0.176539 0.459835 11.00000 0.03187 0.03435 =
0.03484 -0.00407 0.00141 -0.00288
C19 1 0.882514 0.137638 0.478690 11.00000 0.03912 0.04682 =
0.04191 -0.00142 -0.00098 -0.00236
AFIX 43
H19 2 0.932565 0.166306 0.463427 11.00000 -1.20000
AFIX 0
C20 1 0.888292 0.058076 0.519191 11.00000 0.04879 0.05161 =
0.04765 -0.00232 -0.00943 0.00364
AFIX 43
H20 2 0.941581 0.032432 0.531525 11.00000 -1.20000
AFIX 0
C21 1 0.815938 0.016788 0.541266 11.00000 0.06882 0.04686 =
0.03642 -0.00027 -0.00191 -0.00240
AFIX 43
H21 2 0.819338 -0.038706 0.568935 11.00000 -1.20000
AFIX 0
C22 1 0.738538 0.054903 0.523755 11.00000 0.05072 0.04769 =
0.04201 -0.00226 0.01011 -0.00898
AFIX 43
H22 2 0.688868 0.025733 0.539293 11.00000 -1.20000
AFIX 0
C23 1 0.733207 0.136094 0.483325 11.00000 0.03751 0.03723 =
0.03661 -0.00318 -0.00038 0.00009
C24 1 0.582914 0.130224 0.485409 11.00000 0.03856 0.07404 =
0.07556 -0.00849 0.01521 -0.00618
AFIX 137
H24A 2 0.582395 0.006106 0.486419 11.00000 -1.50000
H24B 2 0.534823 0.170386 0.468231 11.00000 -1.50000
H24C 2 0.579385 0.175322 0.515382 11.00000 -1.50000
AFIX 0
N 3 0.541679 0.292797 0.193381 11.00000 0.03441 0.04622 =
0.03829 0.00363 -0.00317 -0.00481
O1 4 0.867525 0.355517 0.407374 11.00000 0.03884 0.05586 =
0.04758 0.00223 0.00252 -0.00993
O2 4 0.659100 0.187005 0.465238 11.00000 0.03356 0.06245 =
0.04925 0.00097 0.00639 -0.00220
HKLF 4
REM HLCL-66 in Pbca
REM R1 = 0.0475 for 1845 Fo > 4sig(Fo) and 0.1193 for all 3352 data
REM 246 parameters refined using 0 restraints
END
;
_cod_data_source_file lh5681sup1.cif
_cod_data_source_block I
_cod_original_formula_sum 'C24 H21 N1 O2'
_cod_database_code 2238990
_cod_database_fobs_code 2238990
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.58107(13) 0.4180(3) 0.16865(7) 0.0365(5) Uani d 1
C C2 0.55972(13) 0.4813(3) 0.12727(7) 0.0425(6) Uani d 1
H H2 0.5137 0.4363 0.1112 0.051 Uiso calc 1
C C3 0.60792(14) 0.6114(3) 0.11058(7) 0.0477(6) Uani d 1
H H3 0.5943 0.6574 0.0826 0.057 Uiso calc 1
C C4 0.67642(14) 0.6775(3) 0.13385(7) 0.0492(6) Uani d 1
H H4 0.7089 0.7663 0.1214 0.059 Uiso calc 1
C C5 0.69696(13) 0.6144(3) 0.17475(7) 0.0451(6) Uani d 1
H H5 0.7433 0.6594 0.1906 0.054 Uiso calc 1
C C6 0.64896(12) 0.4840(3) 0.19261(7) 0.0345(5) Uani d 1
C C7 0.65009(12) 0.3956(3) 0.23405(7) 0.0339(5) Uani d 1
C C8 0.70128(12) 0.4038(3) 0.27101(7) 0.0362(5) Uani d 1
H H8 0.7475 0.4797 0.2714 0.043 Uiso calc 1
C C9 0.68545(12) 0.3019(3) 0.30752(7) 0.0355(5) Uani d 1
C C10 0.61672(12) 0.1890(3) 0.30591(7) 0.0404(6) Uani d 1
H H10 0.6051 0.1203 0.3308 0.048 Uiso calc 1
C C11 0.56615(13) 0.1754(3) 0.26952(7) 0.0410(6) Uani d 1
H H11 0.5207 0.0976 0.269 0.049 Uiso calc 1
C C12 0.58310(12) 0.2786(3) 0.23322(7) 0.0350(5) Uani d 1
C C13 0.47419(13) 0.1832(3) 0.17763(7) 0.0499(7) Uani d 1
H H13A 0.4331 0.2524 0.161 0.06 Uiso calc 1
H H13B 0.4447 0.1334 0.2032 0.06 Uiso calc 1
C C14 0.50550(18) 0.0424(3) 0.14849(9) 0.0828(9) Uani d 1
H H14A 0.5365 0.0907 0.1236 0.124 Uiso calc 1
H H14B 0.4577 -0.0232 0.1375 0.124 Uiso calc 1
H H14C 0.5427 -0.032 0.1654 0.124 Uiso calc 1
C C15 0.74185(12) 0.3152(3) 0.34485(7) 0.0372(5) Uani d 1
H H15 0.7867 0.3933 0.3413 0.045 Uiso calc 1
C C16 0.74025(12) 0.2341(3) 0.38357(7) 0.0379(5) Uani d 1
H H16 0.696 0.1573 0.39 0.045 Uiso calc 1
C C17 0.80689(13) 0.2638(3) 0.41605(7) 0.0369(5) Uani d 1
C C18 0.80572(12) 0.1765(3) 0.45984(7) 0.0337(5) Uani d 1
C C19 0.88251(13) 0.1376(3) 0.47869(7) 0.0426(6) Uani d 1
H H19 0.9326 0.1663 0.4634 0.051 Uiso calc 1
C C20 0.88829(15) 0.0581(3) 0.51919(8) 0.0493(6) Uani d 1
H H20 0.9416 0.0324 0.5315 0.059 Uiso calc 1
C C21 0.81594(16) 0.0168(3) 0.54127(7) 0.0507(6) Uani d 1
H H21 0.8193 -0.0387 0.5689 0.061 Uiso calc 1
C C22 0.73854(15) 0.0549(3) 0.52376(7) 0.0468(6) Uani d 1
H H22 0.6889 0.0257 0.5393 0.056 Uiso calc 1
C C23 0.73321(13) 0.1361(3) 0.48332(7) 0.0371(5) Uani d 1
C C24 0.58291(13) 0.1302(3) 0.48541(8) 0.0627(7) Uani d 1
H H24A 0.5824 0.0061 0.4864 0.094 Uiso calc 1
H H24B 0.5348 0.1704 0.4682 0.094 Uiso calc 1
H H24C 0.5794 0.1753 0.5154 0.094 Uiso calc 1
N N 0.54168(10) 0.2928(2) 0.19338(6) 0.0396(5) Uani d 1
O O1 0.86753(9) 0.35552(18) 0.40737(5) 0.0474(4) Uani d 1
O O2 0.65910(8) 0.18701(19) 0.46524(5) 0.0484(4) Uani d 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0346(12) 0.0392(13) 0.0359(13) 0.0007(11) 0.0055(11) 0.0002(12)
C2 0.0404(14) 0.0500(15) 0.0371(14) 0.0000(12) 0.0011(11) -0.0038(12)
C3 0.0535(15) 0.0543(16) 0.0352(14) 0.0037(14) 0.0009(12) 0.0049(13)
C4 0.0544(15) 0.0485(16) 0.0447(15) -0.0076(13) 0.0043(13) 0.0064(13)
C5 0.0425(14) 0.0499(15) 0.0430(15) -0.0075(12) -0.0024(12) 0.0011(13)
C6 0.0329(12) 0.0359(13) 0.0346(13) 0.0000(11) 0.0021(11) -0.0020(11)
C7 0.0335(12) 0.0341(13) 0.0340(13) 0.0005(11) 0.0010(11) -0.0009(11)
C8 0.0314(12) 0.0358(13) 0.0413(14) -0.0022(11) 0.0022(11) -0.0006(12)
C9 0.0332(12) 0.0354(13) 0.0379(14) 0.0015(11) 0.0005(10) -0.0002(11)
C10 0.0380(13) 0.0439(14) 0.0393(14) -0.0003(12) 0.0020(11) 0.0048(12)
C11 0.0344(12) 0.0417(14) 0.0467(15) -0.0083(11) 0.0011(11) 0.0041(12)
C12 0.0316(12) 0.0381(13) 0.0353(13) 0.0015(11) 0.0017(10) -0.0004(11)
C13 0.0438(14) 0.0623(17) 0.0436(15) -0.0172(13) -0.0059(11) 0.0042(13)
C14 0.098(2) 0.063(2) 0.087(2) -0.0234(17) 0.0054(18) -0.0195(17)
C15 0.0338(12) 0.0378(13) 0.0399(14) -0.0011(11) 0.0003(11) 0.0002(11)
C16 0.0325(12) 0.0418(14) 0.0392(13) -0.0034(11) 0.0015(11) -0.0002(12)
C17 0.0333(12) 0.0384(13) 0.0391(14) 0.0014(12) 0.0042(11) -0.0034(11)
C18 0.0319(12) 0.0344(13) 0.0348(13) -0.0029(11) 0.0014(10) -0.0041(10)
C19 0.0391(13) 0.0468(15) 0.0419(15) -0.0024(12) -0.0010(11) -0.0014(12)
C20 0.0488(15) 0.0516(16) 0.0477(16) 0.0036(13) -0.0094(13) -0.0023(13)
C21 0.0688(18) 0.0469(16) 0.0364(14) -0.0024(15) -0.0019(14) -0.0003(12)
C22 0.0507(16) 0.0477(15) 0.0420(15) -0.0090(13) 0.0101(12) -0.0023(12)
C23 0.0375(14) 0.0372(13) 0.0366(14) 0.0001(11) -0.0004(11) -0.0032(11)
C24 0.0386(14) 0.0740(18) 0.0756(18) -0.0062(14) 0.0152(13) -0.0085(15)
N 0.0344(10) 0.0462(12) 0.0383(11) -0.0048(10) -0.0032(9) 0.0036(10)
O1 0.0388(9) 0.0559(10) 0.0476(10) -0.0099(8) 0.0025(7) 0.0022(8)
O2 0.0336(9) 0.0624(11) 0.0493(10) -0.0022(8) 0.0064(7) 0.0010(8)
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 0 '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 0.006 '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
N C1 C2 129.15(19)
N C1 C6 109.29(18)
C2 C1 C6 121.5(2)
C3 C2 C1 117.5(2)
C3 C2 H2 121.2
C1 C2 H2 121.2
C2 C3 C4 121.7(2)
C2 C3 H3 119.2
C4 C3 H3 119.2
C5 C4 C3 120.4(2)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C6 119.2(2)
C4 C5 H5 120.4
C6 C5 H5 120.4
C5 C6 C1 119.7(2)
C5 C6 C7 133.8(2)
C1 C6 C7 106.50(18)
C8 C7 C12 119.25(18)
C8 C7 C6 133.78(19)
C12 C7 C6 106.96(17)
C7 C8 C9 120.71(19)
C7 C8 H8 119.6
C9 C8 H8 119.6
C8 C9 C10 118.47(19)
C8 C9 C15 117.97(18)
C10 C9 C15 123.55(19)
C11 C10 C9 122.2(2)
C11 C10 H10 118.9
C9 C10 H10 118.9
C10 C11 C12 118.51(19)
C10 C11 H11 120.7
C12 C11 H11 120.7
N C12 C11 130.25(19)
N C12 C7 108.86(17)
C11 C12 C7 120.86(19)
N C13 C14 112.70(19)
N C13 H13A 109.1
C14 C13 H13A 109.1
N C13 H13B 109.1
C14 C13 H13B 109.1
H13A C13 H13B 107.8
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C16 C15 C9 129.8(2)
C16 C15 H15 115.1
C9 C15 H15 115.1
C15 C16 C17 120.0(2)
C15 C16 H16 120
C17 C16 H16 120
O1 C17 C16 121.00(19)
O1 C17 C18 117.93(18)
C16 C17 C18 121.00(19)
C19 C18 C23 118.0(2)
C19 C18 C17 117.27(19)
C23 C18 C17 124.75(19)
C20 C19 C18 121.8(2)
C20 C19 H19 119.1
C18 C19 H19 119.1
C21 C20 C19 119.1(2)
C21 C20 H20 120.5
C19 C20 H20 120.5
C20 C21 C22 120.7(2)
C20 C21 H21 119.6
C22 C21 H21 119.6
C21 C22 C23 119.9(2)
C21 C22 H22 120.1
C23 C22 H22 120.1
O2 C23 C22 123.10(19)
O2 C23 C18 116.32(18)
C22 C23 C18 120.5(2)
O2 C24 H24A 109.5
O2 C24 H24B 109.5
H24A C24 H24B 109.5
O2 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
C12 N C1 108.39(16)
C12 N C13 126.16(18)
C1 N C13 125.12(18)
C23 O2 C24 117.99(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N 1.391(2) n
C1 C2 1.396(3) ?
C1 C6 1.404(3) n
C2 C3 1.379(3) ?
C2 H2 0.95 ?
C3 C4 1.402(3) ?
C3 H3 0.95 ?
C4 C5 1.379(3) ?
C4 H4 0.95 ?
C5 C6 1.393(3) ?
C5 H5 0.95 ?
C6 C7 1.440(3) n
C7 C8 1.390(3) ?
C7 C12 1.411(3) n
C8 C9 1.394(3) ?
C8 H8 0.95 ?
C9 C10 1.412(3) ?
C9 C15 1.452(3) n
C10 C11 1.373(3) ?
C10 H10 0.95 ?
C11 C12 1.398(3) ?
C11 H11 0.95 ?
C12 N 1.384(2) n
C13 N 1.461(2) n
C13 C14 1.506(3) ?
C13 H13A 0.99 ?
C13 H13B 0.99 ?
C14 H14A 0.98 ?
C14 H14B 0.98 ?
C14 H14C 0.98 ?
C15 C16 1.340(3) n
C15 H15 0.95 ?
C16 C17 1.469(3) n
C16 H16 0.95 ?
C17 O1 1.236(2) n
C17 C18 1.499(3) n
C18 C19 1.386(3) ?
C18 C23 1.395(3) ?
C19 C20 1.385(3) ?
C19 H19 0.95 ?
C20 C21 1.373(3) ?
C20 H20 0.95 ?
C21 C22 1.377(3) ?
C21 H21 0.95 ?
C22 C23 1.389(3) ?
C22 H22 0.95 ?
C23 O2 1.363(2) ?
C24 O2 1.432(2) ?
C24 H24A 0.98 ?
C24 H24B 0.98 ?
C24 H24C 0.98 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2 O1 6_556 0.95 2.48 3.387(3) 159.8
C13 H13A O1 6_556 0.99 2.47 3.379(3) 153.1
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
N C1 C2 C3 177.6(2)
C6 C1 C2 C3 0.1(3)
C1 C2 C3 C4 0.6(3)
C2 C3 C4 C5 -0.7(3)
C3 C4 C5 C6 0.1(3)
C4 C5 C6 C1 0.5(3)
C4 C5 C6 C7 -176.7(2)
N C1 C6 C5 -178.57(18)
C2 C1 C6 C5 -0.6(3)
N C1 C6 C7 -0.6(2)
C2 C1 C6 C7 177.29(18)
C5 C6 C7 C8 -2.6(4)
C1 C6 C7 C8 179.9(2)
C5 C6 C7 C12 178.0(2)
C1 C6 C7 C12 0.5(2)
C12 C7 C8 C9 -2.0(3)
C6 C7 C8 C9 178.7(2)
C7 C8 C9 C10 0.6(3)
C7 C8 C9 C15 179.30(18)
C8 C9 C10 C11 0.9(3)
C15 C9 C10 C11 -177.79(19)
C9 C10 C11 C12 -0.8(3)
C10 C11 C12 N -178.5(2)
C10 C11 C12 C7 -0.7(3)
C8 C7 C12 N -179.69(17)
C6 C7 C12 N -0.2(2)
C8 C7 C12 C11 2.1(3)
C6 C7 C12 C11 -178.43(18)
C8 C9 C15 C16 179.2(2)
C10 C9 C15 C16 -2.1(3)
C9 C15 C16 C17 177.50(19)
C15 C16 C17 O1 -4.2(3)
C15 C16 C17 C18 179.06(18)
O1 C17 C18 C19 -29.0(3)
C16 C17 C18 C19 147.86(19)
O1 C17 C18 C23 149.2(2)
C16 C17 C18 C23 -33.9(3)
C23 C18 C19 C20 1.2(3)
C17 C18 C19 C20 179.58(19)
C18 C19 C20 C21 -0.1(3)
C19 C20 C21 C22 -0.6(3)
C20 C21 C22 C23 0.0(3)
C21 C22 C23 O2 -175.86(19)
C21 C22 C23 C18 1.3(3)
C19 C18 C23 O2 175.48(18)
C17 C18 C23 O2 -2.7(3)
C19 C18 C23 C22 -1.8(3)
C17 C18 C23 C22 179.97(19)
C11 C12 N C1 177.8(2)
C7 C12 N C1 -0.2(2)
C11 C12 N C13 -8.5(3)
C7 C12 N C13 173.47(18)
C2 C1 N C12 -177.2(2)
C6 C1 N C12 0.5(2)
C2 C1 N C13 9.1(3)
C6 C1 N C13 -173.23(18)
C14 C13 N C12 -95.3(2)
C14 C13 N C1 77.3(3)
C22 C23 O2 C24 -10.3(3)
C18 C23 O2 C24 172.48(19)