#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:16:27 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257986 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240373.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_7240373
loop_
_publ_author_name
'Krishna Reddy, Singarajanahalli Mundarinti'
'Suresh, Pavithira'
'Thamotharan, Subbiah'
'Nanubolu, Jagadeesh Babu'
'Suresh, Surisetti'
'Selva Ganesan, Subramaniapillai'
_publ_section_title
;
Substrate controlled, regioselective carbopalladation for the one-pot
synthesis of C4-substituted tetrahydroisoquinoline analogues
;
_journal_issue 27
_journal_name_full 'RSC Advances'
_journal_page_first 15794
_journal_page_last 15799
_journal_paper_doi 10.1039/D0RA01539C
_journal_volume 10
_journal_year 2020
_chemical_formula_moiety 'C24 H23 N O'
_chemical_formula_sum 'C24 H23 N O'
_chemical_formula_weight 341.43
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_Hall '-P 1'
_space_group_name_H-M_alt 'P -1'
_atom_sites_solution_hydrogens geom
_audit_creation_method SHELXL-2018/3
_audit_update_record
;
2019-04-29 deposited with the CCDC. 2020-04-13 downloaded from the CCDC.
;
_cell_angle_alpha 79.554(4)
_cell_angle_beta 84.737(4)
_cell_angle_gamma 81.243(5)
_cell_formula_units_Z 2
_cell_length_a 6.1269(7)
_cell_length_b 9.0770(12)
_cell_length_c 17.366(2)
_cell_measurement_reflns_used 8290
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 30.250
_cell_measurement_theta_min 2.3905
_cell_volume 936.7(2)
_computing_cell_refinement 'SAINT (Bruker, 2016)'
_computing_data_collection 'APEX3 (Bruker, 2016)'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type 'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method '\w and \f'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0473
_diffrn_reflns_av_unetI/netI 0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_number 20789
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.496
_diffrn_reflns_theta_min 2.304
_exptl_absorpt_coefficient_mu 0.073
_exptl_absorpt_correction_T_max 0.7461
_exptl_absorpt_correction_T_min 0.6020
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'SADABS 2014/5'
_exptl_crystal_density_diffrn 1.211
_exptl_crystal_description block
_exptl_crystal_F_000 364
_exptl_crystal_size_max 0.400
_exptl_crystal_size_mid 0.290
_exptl_crystal_size_min 0.180
_refine_diff_density_max 0.170
_refine_diff_density_min -0.196
_refine_diff_density_rms 0.039
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.158
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 236
_refine_ls_number_reflns 4289
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.158
_refine_ls_R_factor_all 0.0681
_refine_ls_R_factor_gt 0.0466
_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/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1479
_refine_ls_wR_factor_ref 0.1672
_reflns_Friedel_coverage 0.000
_reflns_number_gt 3140
_reflns_number_total 4289
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file d0ra01539c2.cif
_cod_data_source_block KA640_0m
_cod_depositor_comments 'Adding full bibliography for 7240373.cif.'
_cod_original_cell_volume 936.6(2)
_cod_database_code 7240373
_shelx_shelxl_version_number 2018/3
_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_min 0.971
_shelx_estimated_absorpt_t_max 0.987
_shelx_res_file
;
TITL KA640_0m_a.res in P-1
KA640_0m.res
created by SHELXL-2018/3 at 17:40:46 on 29-Apr-2019
CELL 0.71073 6.1269 9.0770 17.3656 79.5540 84.7372 81.2434
ZERR 2.00 0.0007 0.0012 0.0023 0.0043 0.0043 0.0045
LATT 1
SFAC C H N O
UNIT 48 46 2 2
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
TEMP 20.000
ACTA
L.S. 4
FMAP 2
PLAN 20
OMIT -3 55
HTAB
BOND $H
CONF
SIZE 0.40 0.29 0.18
WGHT 0.100000
FVAR 1.16019
C1 1 0.346576 0.429192 0.800410 11.00000 0.04673 0.04218 =
0.03899 -0.00131 -0.00004 -0.00117
AFIX 23
H1A 2 0.226501 0.381267 0.787726 11.00000 -1.20000
H1B 2 0.324387 0.438543 0.855438 11.00000 -1.20000
AFIX 0
C2 1 0.561691 0.330764 0.787357 11.00000 0.04936 0.03565 =
0.03617 -0.00929 -0.00834 0.00008
C3 1 0.621863 0.203552 0.843130 11.00000 0.07222 0.04425 =
0.03813 -0.00298 -0.00548 0.00663
AFIX 43
H3 2 0.528071 0.181941 0.887677 11.00000 -1.20000
AFIX 0
C4 1 0.817240 0.108922 0.833831 11.00000 0.08119 0.04220 =
0.05002 -0.00429 -0.01888 0.01468
AFIX 43
H4 2 0.855048 0.024624 0.871795 11.00000 -1.20000
AFIX 0
C5 1 0.955394 0.140274 0.768041 11.00000 0.05820 0.04636 =
0.06168 -0.01555 -0.01648 0.01571
AFIX 43
H5 2 1.087586 0.076935 0.761413 11.00000 -1.20000
AFIX 0
C6 1 0.899282 0.265628 0.711437 11.00000 0.04469 0.04516 =
0.04933 -0.01484 -0.00770 0.00178
AFIX 43
H6 2 0.994359 0.285185 0.667033 11.00000 -1.20000
AFIX 0
C7 1 0.701491 0.363694 0.719879 11.00000 0.03977 0.03498 =
0.03697 -0.01206 -0.01021 -0.00172
C8 1 0.632737 0.495863 0.659081 11.00000 0.03474 0.03721 =
0.03255 -0.01181 -0.00713 -0.00325
C9 1 0.395995 0.567221 0.670358 11.00000 0.03570 0.04047 =
0.03205 -0.00527 -0.00493 -0.00241
AFIX 23
H9A 2 0.375176 0.667001 0.638344 11.00000 -1.20000
H9B 2 0.298426 0.506257 0.653497 11.00000 -1.20000
AFIX 0
C10 1 0.119002 0.667110 0.761760 11.00000 0.03727 0.04635 =
0.03962 -0.00515 -0.00300 0.00464
AFIX 23
H10A 2 0.009522 0.613171 0.746404 11.00000 -1.20000
H10B 2 0.114712 0.763798 0.726883 11.00000 -1.20000
AFIX 0
C11 1 0.060258 0.693943 0.845001 11.00000 0.03877 0.03993 =
0.03999 -0.00210 -0.00129 0.00807
C12 1 -0.135881 0.656756 0.884344 11.00000 0.05015 0.06340 =
0.05464 -0.00831 0.00693 -0.00480
AFIX 43
H12 2 -0.232495 0.614128 0.859420 11.00000 -1.20000
AFIX 0
C13 1 -0.189926 0.682389 0.960574 11.00000 0.06457 0.08942 =
0.05559 -0.00720 0.01953 -0.00510
AFIX 43
H13 2 -0.322073 0.656586 0.986429 11.00000 -1.20000
AFIX 0
C14 1 -0.049761 0.745451 0.997914 11.00000 0.07767 0.08443 =
0.04188 -0.01271 0.00552 0.01390
AFIX 43
H14 2 -0.086566 0.762753 1.048979 11.00000 -1.20000
AFIX 0
C15 1 0.145193 0.783022 0.959714 11.00000 0.06817 0.07732 =
0.05289 -0.02129 -0.01297 0.00620
AFIX 43
H15 2 0.241268 0.825383 0.985009 11.00000 -1.20000
AFIX 0
C16 1 0.199348 0.757953 0.883407 11.00000 0.04728 0.06452 =
0.04682 -0.01111 -0.00132 0.00094
AFIX 43
H16 2 0.331270 0.784661 0.857760 11.00000 -1.20000
AFIX 0
C17 1 0.770552 0.549737 0.599888 11.00000 0.03174 0.04468 =
0.04036 -0.01164 -0.00570 -0.00159
AFIX 43
H17 2 0.915769 0.501469 0.599958 11.00000 -1.20000
AFIX 0
C18 1 0.721308 0.675811 0.534646 11.00000 0.03339 0.04168 =
0.03365 -0.01233 0.00194 -0.00511
C19 1 0.875148 0.777277 0.509423 11.00000 0.03120 0.05959 =
0.04209 -0.01171 -0.00181 -0.01004
AFIX 43
H19 2 1.008037 0.762202 0.533540 11.00000 -1.20000
AFIX 0
C20 1 0.834223 0.898244 0.450011 11.00000 0.04077 0.05222 =
0.04342 -0.00875 0.00415 -0.01915
AFIX 43
H20 2 0.937476 0.965108 0.435286 11.00000 -1.20000
AFIX 0
C21 1 0.639385 0.921161 0.411832 11.00000 0.04278 0.03825 =
0.03168 -0.00927 0.00517 -0.00760
C22 1 0.487863 0.820051 0.433295 11.00000 0.03615 0.04274 =
0.03637 -0.00986 -0.00381 -0.00725
AFIX 43
H22 2 0.358999 0.832435 0.407006 11.00000 -1.20000
AFIX 0
C23 1 0.530010 0.700006 0.494412 11.00000 0.03712 0.03998 =
0.03812 -0.00980 -0.00047 -0.01196
AFIX 43
H23 2 0.426359 0.633378 0.508932 11.00000 -1.20000
AFIX 0
C24 1 0.420371 1.072632 0.311789 11.00000 0.06767 0.05720 =
0.04762 0.00343 -0.01128 -0.01129
AFIX 137
H24A 2 0.422728 1.163442 0.273684 11.00000 -1.50000
H24B 2 0.292965 1.084251 0.347838 11.00000 -1.50000
H24C 2 0.413613 0.989051 0.285632 11.00000 -1.50000
AFIX 0
N1 3 0.339236 0.579736 0.752993 11.00000 0.03695 0.03759 =
0.03093 -0.00457 -0.00235 0.00292
O1 4 0.615038 1.044798 0.353455 11.00000 0.05609 0.04851 =
0.04960 0.00396 -0.00352 -0.01475
HKLF 4 1 1 0 0 0 1 0 0 0 1
REM KA640_0m_a.res in P-1
REM wR2 = 0.1672, GooF = S = 1.158, Restrained GooF = 1.158 for all data
REM R1 = 0.0466 for 3140 Fo > 4sig(Fo) and 0.0681 for all 4289 data
REM 236 parameters refined using 0 restraints
END
WGHT 0.0624 0.1899
REM Instructions for potential hydrogen bonds
EQIV $1 -x+1, -y+2, -z+1
HTAB C9 O1_$1
REM Highest difference peak 0.170, deepest hole -0.196, 1-sigma level 0.039
Q1 1 0.8203 0.7054 0.5076 11.00000 0.05 0.17
Q2 1 0.5332 0.9025 0.4389 11.00000 0.05 0.17
Q3 1 0.6939 0.4461 0.6990 11.00000 0.05 0.16
Q4 1 0.1944 0.8085 0.7344 11.00000 0.05 0.15
Q5 1 0.4769 0.5747 0.7698 11.00000 0.05 0.15
Q6 1 0.4437 0.6332 0.7617 11.00000 0.05 0.15
Q7 1 0.8577 0.8070 0.4596 11.00000 0.05 0.14
Q8 1 0.4326 0.1516 0.8806 11.00000 0.05 0.13
Q9 1 0.6202 0.8331 0.4094 11.00000 0.05 0.13
Q10 1 0.9955 0.4462 0.5827 11.00000 0.05 0.13
Q11 1 0.7738 1.0779 0.3096 11.00000 0.05 0.13
Q12 1 0.2224 0.3831 0.8493 11.00000 0.05 0.12
Q13 1 -0.0642 0.6565 0.9767 11.00000 0.05 0.12
Q14 1 0.8367 0.3435 0.7296 11.00000 0.05 0.12
Q15 1 0.9814 0.3331 0.6051 11.00000 0.05 0.11
Q16 1 0.4262 0.4848 0.8600 11.00000 0.05 0.11
Q17 1 0.8068 -0.0594 0.8825 11.00000 0.05 0.11
Q18 1 0.5455 0.2405 0.7993 11.00000 0.05 0.11
Q19 1 0.6729 0.6644 0.5020 11.00000 0.05 0.11
Q20 1 0.7339 -0.0984 0.9115 11.00000 0.05 0.11
;
_shelx_res_checksum 75023
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.3466(2) 0.42919(16) 0.80041(8) 0.0440(3) Uani 1 1 d . . . . .
H1A H 0.226501 0.381267 0.787726 0.053 Uiso 1 1 calc R U . . .
H1B H 0.324387 0.438543 0.855438 0.053 Uiso 1 1 calc R U . . .
C2 C 0.5617(2) 0.33076(15) 0.78736(8) 0.0403(3) Uani 1 1 d . . . . .
C3 C 0.6219(3) 0.20355(17) 0.84313(9) 0.0535(4) Uani 1 1 d . . . . .
H3 H 0.528071 0.181941 0.887677 0.064 Uiso 1 1 calc R U . . .
C4 C 0.8172(3) 0.10892(18) 0.83383(9) 0.0598(5) Uani 1 1 d . . . . .
H4 H 0.855048 0.024624 0.871795 0.072 Uiso 1 1 calc R U . . .
C5 C 0.9554(3) 0.14027(18) 0.76804(10) 0.0562(4) Uani 1 1 d . . . . .
H5 H 1.087586 0.076935 0.761413 0.067 Uiso 1 1 calc R U . . .
C6 C 0.8993(2) 0.26563(17) 0.71144(9) 0.0461(4) Uani 1 1 d . . . . .
H6 H 0.994359 0.285185 0.667033 0.055 Uiso 1 1 calc R U . . .
C7 C 0.7015(2) 0.36369(14) 0.71988(7) 0.0364(3) Uani 1 1 d . . . . .
C8 C 0.6327(2) 0.49586(14) 0.65908(7) 0.0340(3) Uani 1 1 d . . . . .
C9 C 0.3960(2) 0.56722(15) 0.67036(7) 0.0363(3) Uani 1 1 d . . . . .
H9A H 0.375176 0.667001 0.638344 0.044 Uiso 1 1 calc R U . . .
H9B H 0.298426 0.506257 0.653497 0.044 Uiso 1 1 calc R U . . .
C10 C 0.1190(2) 0.66711(16) 0.76176(8) 0.0424(3) Uani 1 1 d . . . . .
H10A H 0.009522 0.613171 0.746404 0.051 Uiso 1 1 calc R U . . .
H10B H 0.114712 0.763798 0.726883 0.051 Uiso 1 1 calc R U . . .
C11 C 0.0603(2) 0.69394(16) 0.84500(8) 0.0417(3) Uani 1 1 d . . . . .
C12 C -0.1359(3) 0.65676(19) 0.88434(10) 0.0573(4) Uani 1 1 d . . . . .
H12 H -0.232495 0.614128 0.859420 0.069 Uiso 1 1 calc R U . . .
C13 C -0.1899(3) 0.6824(2) 0.96057(10) 0.0726(6) Uani 1 1 d . . . . .
H13 H -0.322073 0.656586 0.986429 0.087 Uiso 1 1 calc R U . . .
C14 C -0.0498(3) 0.7455(2) 0.99791(10) 0.0710(5) Uani 1 1 d . . . . .
H14 H -0.086566 0.762753 1.048979 0.085 Uiso 1 1 calc R U . . .
C15 C 0.1452(3) 0.7830(2) 0.95971(10) 0.0660(5) Uani 1 1 d . . . . .
H15 H 0.241268 0.825383 0.985009 0.079 Uiso 1 1 calc R U . . .
C16 C 0.1993(3) 0.75795(19) 0.88341(9) 0.0537(4) Uani 1 1 d . . . . .
H16 H 0.331270 0.784661 0.857760 0.064 Uiso 1 1 calc R U . . .
C17 C 0.7706(2) 0.54974(15) 0.59989(7) 0.0386(3) Uani 1 1 d . . . . .
H17 H 0.915769 0.501469 0.599958 0.046 Uiso 1 1 calc R U . . .
C18 C 0.7213(2) 0.67581(15) 0.53465(7) 0.0358(3) Uani 1 1 d . . . . .
C19 C 0.8751(2) 0.77728(17) 0.50942(8) 0.0435(3) Uani 1 1 d . . . . .
H19 H 1.008037 0.762202 0.533540 0.052 Uiso 1 1 calc R U . . .
C20 C 0.8342(2) 0.89824(17) 0.45001(8) 0.0445(4) Uani 1 1 d . . . . .
H20 H 0.937476 0.965108 0.435286 0.053 Uiso 1 1 calc R U . . .
C21 C 0.6394(2) 0.92116(15) 0.41183(7) 0.0374(3) Uani 1 1 d . . . . .
C22 C 0.4879(2) 0.82005(15) 0.43329(8) 0.0377(3) Uani 1 1 d . . . . .
H22 H 0.358999 0.832435 0.407006 0.045 Uiso 1 1 calc R U . . .
C23 C 0.5300(2) 0.70001(15) 0.49441(7) 0.0374(3) Uani 1 1 d . . . . .
H23 H 0.426359 0.633378 0.508932 0.045 Uiso 1 1 calc R U . . .
C24 C 0.4204(3) 1.0726(2) 0.31179(9) 0.0583(4) Uani 1 1 d . . . . .
H24A H 0.422728 1.163442 0.273684 0.087 Uiso 1 1 calc R U . . .
H24B H 0.292965 1.084251 0.347838 0.087 Uiso 1 1 calc R U . . .
H24C H 0.413613 0.989051 0.285632 0.087 Uiso 1 1 calc R U . . .
N1 N 0.33924(17) 0.57974(12) 0.75299(6) 0.0362(3) Uani 1 1 d . . . . .
O1 O 0.61504(17) 1.04480(12) 0.35346(6) 0.0522(3) Uani 1 1 d . . . . .
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
C1 0.0467(8) 0.0422(8) 0.0390(7) -0.0013(6) 0.0000(6) -0.0012(6)
C2 0.0494(8) 0.0357(7) 0.0362(7) -0.0093(5) -0.0083(6) 0.0001(6)
C3 0.0722(11) 0.0443(8) 0.0381(8) -0.0030(6) -0.0055(7) 0.0066(7)
C4 0.0812(12) 0.0422(8) 0.0500(9) -0.0043(7) -0.0189(8) 0.0147(8)
C5 0.0582(10) 0.0464(9) 0.0617(10) -0.0155(7) -0.0165(8) 0.0157(7)
C6 0.0447(8) 0.0452(8) 0.0493(8) -0.0148(6) -0.0077(6) 0.0018(6)
C7 0.0398(7) 0.0350(7) 0.0370(7) -0.0121(5) -0.0102(5) -0.0017(5)
C8 0.0347(7) 0.0372(7) 0.0325(6) -0.0118(5) -0.0071(5) -0.0032(5)
C9 0.0357(7) 0.0405(7) 0.0321(7) -0.0053(5) -0.0049(5) -0.0024(5)
C10 0.0373(7) 0.0464(8) 0.0396(7) -0.0052(6) -0.0030(5) 0.0046(6)
C11 0.0388(7) 0.0399(7) 0.0400(7) -0.0021(6) -0.0013(6) 0.0081(6)
C12 0.0502(9) 0.0634(10) 0.0546(10) -0.0083(8) 0.0069(7) -0.0048(7)
C13 0.0646(11) 0.0894(14) 0.0556(11) -0.0072(10) 0.0195(9) -0.0051(10)
C14 0.0777(13) 0.0844(13) 0.0419(9) -0.0127(9) 0.0055(8) 0.0139(10)
C15 0.0682(11) 0.0773(12) 0.0529(10) -0.0213(9) -0.0130(8) 0.0062(9)
C16 0.0473(9) 0.0645(10) 0.0468(9) -0.0111(7) -0.0013(6) 0.0009(7)
C17 0.0317(7) 0.0447(8) 0.0404(7) -0.0116(6) -0.0057(5) -0.0016(5)
C18 0.0334(7) 0.0417(7) 0.0336(6) -0.0123(5) 0.0019(5) -0.0051(5)
C19 0.0312(7) 0.0596(9) 0.0421(7) -0.0117(7) -0.0018(5) -0.0100(6)
C20 0.0408(8) 0.0522(9) 0.0434(8) -0.0087(6) 0.0041(6) -0.0191(6)
C21 0.0428(7) 0.0383(7) 0.0317(6) -0.0093(5) 0.0052(5) -0.0076(6)
C22 0.0361(7) 0.0427(8) 0.0364(7) -0.0099(6) -0.0038(5) -0.0072(6)
C23 0.0371(7) 0.0400(7) 0.0381(7) -0.0098(6) -0.0005(5) -0.0120(6)
C24 0.0677(11) 0.0572(10) 0.0476(9) 0.0034(7) -0.0113(7) -0.0113(8)
N1 0.0369(6) 0.0376(6) 0.0309(6) -0.0046(4) -0.0024(4) 0.0029(5)
O1 0.0561(6) 0.0485(6) 0.0496(6) 0.0040(5) -0.0035(5) -0.0147(5)
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'
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
N1 C1 C2 112.44(11) . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C7 119.62(13) . . ?
C3 C2 C1 119.14(13) . . ?
C7 C2 C1 121.24(12) . . ?
C4 C3 C2 121.49(15) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 119.35(14) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.41(14) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 121.16(14) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 117.98(12) . . ?
C2 C7 C8 119.47(12) . . ?
C6 C7 C8 122.51(12) . . ?
C17 C8 C7 122.94(12) . . ?
C17 C8 C9 122.55(11) . . ?
C7 C8 C9 114.49(11) . . ?
N1 C9 C8 110.55(9) . . ?
N1 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N1 C10 C11 112.15(10) . . ?
N1 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
N1 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C16 C11 C12 118.25(14) . . ?
C16 C11 C10 120.91(12) . . ?
C12 C11 C10 120.83(14) . . ?
C11 C12 C13 120.69(17) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.32(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.70(16) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.10(17) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.93(15) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C8 C17 C18 128.23(12) . . ?
C8 C17 H17 115.9 . . ?
C18 C17 H17 115.9 . . ?
C23 C18 C19 116.74(12) . . ?
C23 C18 C17 123.65(12) . . ?
C19 C18 C17 119.60(12) . . ?
C20 C19 C18 121.62(12) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 120.29(12) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
O1 C21 C22 124.81(12) . . ?
O1 C21 C20 115.63(12) . . ?
C22 C21 C20 119.55(12) . . ?
C21 C22 C23 119.38(12) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C22 C23 C18 122.36(12) . . ?
C22 C23 H23 118.8 . . ?
C18 C23 H23 118.8 . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 C9 109.82(10) . . ?
C1 N1 C10 110.61(10) . . ?
C9 N1 C10 110.11(9) . . ?
C21 O1 C24 118.05(11) . . ?
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
C1 N1 1.4586(16) . ?
C1 C2 1.4989(19) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.3920(18) . ?
C2 C7 1.4010(19) . ?
C3 C4 1.378(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.4031(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.4832(17) . ?
C8 C17 1.3390(18) . ?
C8 C9 1.5065(18) . ?
C9 N1 1.4658(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N1 1.4674(17) . ?
C10 C11 1.5113(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.380(2) . ?
C11 C12 1.384(2) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.4737(18) . ?
C17 H17 0.9300 . ?
C18 C23 1.3879(18) . ?
C18 C19 1.4039(19) . ?
C19 C20 1.3733(19) . ?
C19 H19 0.9300 . ?
C20 C21 1.388(2) . ?
C20 H20 0.9300 . ?
C21 O1 1.3688(15) . ?
C21 C22 1.3838(18) . ?
C22 C23 1.3877(17) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 O1 1.4178(18) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
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 160.97(13) . . . . ?
N1 C1 C2 C7 -19.68(18) . . . . ?
C7 C2 C3 C4 0.3(2) . . . . ?
C1 C2 C3 C4 179.70(14) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C3 C2 C7 C6 -0.13(19) . . . . ?
C1 C2 C7 C6 -179.47(12) . . . . ?
C3 C2 C7 C8 177.59(12) . . . . ?
C1 C2 C7 C8 -1.76(19) . . . . ?
C5 C6 C7 C2 -0.2(2) . . . . ?
C5 C6 C7 C8 -177.81(12) . . . . ?
C2 C7 C8 C17 168.48(13) . . . . ?
C6 C7 C8 C17 -13.91(19) . . . . ?
C2 C7 C8 C9 -10.13(17) . . . . ?
C6 C7 C8 C9 167.47(12) . . . . ?
C17 C8 C9 N1 -135.44(13) . . . . ?
C7 C8 C9 N1 43.19(14) . . . . ?
N1 C10 C11 C16 53.60(17) . . . . ?
N1 C10 C11 C12 -127.25(14) . . . . ?
C16 C11 C12 C13 -0.4(2) . . . . ?
C10 C11 C12 C13 -179.60(15) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C12 C11 C16 C15 0.6(2) . . . . ?
C10 C11 C16 C15 179.80(14) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C7 C8 C17 C18 177.65(11) . . . . ?
C9 C8 C17 C18 -3.8(2) . . . . ?
C8 C17 C18 C23 -41.7(2) . . . . ?
C8 C17 C18 C19 139.56(15) . . . . ?
C23 C18 C19 C20 2.6(2) . . . . ?
C17 C18 C19 C20 -178.57(12) . . . . ?
C18 C19 C20 C21 -1.5(2) . . . . ?
C19 C20 C21 O1 -179.90(12) . . . . ?
C19 C20 C21 C22 -0.9(2) . . . . ?
O1 C21 C22 C23 -179.03(12) . . . . ?
C20 C21 C22 C23 2.1(2) . . . . ?
C21 C22 C23 C18 -0.9(2) . . . . ?
C19 C18 C23 C22 -1.4(2) . . . . ?
C17 C18 C23 C22 179.83(12) . . . . ?
C2 C1 N1 C9 52.77(14) . . . . ?
C2 C1 N1 C10 174.51(11) . . . . ?
C8 C9 N1 C1 -65.43(13) . . . . ?
C8 C9 N1 C10 172.53(10) . . . . ?
C11 C10 N1 C1 63.00(15) . . . . ?
C11 C10 N1 C9 -175.43(11) . . . . ?
C22 C21 O1 C24 0.3(2) . . . . ?
C20 C21 O1 C24 179.22(13) . . . . ?