#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/27/2012770.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2012770
loop_
_publ_author_name
'Deschamps, Jeffrey R.'
'George, Clifford'
'Flippen-Anderson, Judith L.'
_publ_section_title
;(1R)-2-[(3R,4S)-3-Methyl-4-(N-phenyl-N-propionylamino)piperidin-1-yl]-1-phenylethyl
 p-bromobenzoate and
 N-{(3R,4S)-1-[(2S)-2-(4-bromophenyl)-2-hydroxyethyl]-3-methyl-piperidin-4-yl}-N-phenylacrylamide
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o362
_journal_page_last               o364
_journal_paper_doi               10.1107/S0108270102006443
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C30 H33 Br N2 O3'
_chemical_formula_moiety         'C30 H33 Br N2 O3'
_chemical_formula_sum            'C30 H33 Br N2 O3'
_chemical_formula_weight         549.49
_chemical_name_systematic
;
(1R)-2-[(3R,4S)-3-Methyl-4-(N-phenyl-N-propionylamino)pyridyl]-1-
phenylethyl p-bromobenzoate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.2080(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8806(2)
_cell_length_b                   22.4670(5)
_cell_length_c                   11.5313(3)
_cell_measurement_reflns_used    6392
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      66.8
_cell_measurement_theta_min      3.93
_cell_volume                     2816.78(11)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.921
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Bruker CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Gobel mirrors'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13643
_diffrn_reflns_theta_full        67.03
_diffrn_reflns_theta_max         67.03
_diffrn_reflns_theta_min         3.93
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  variable
_diffrn_standards_number         88
_exptl_absorpt_coefficient_mu    2.240
_exptl_absorpt_correction_T_max  0.9307
_exptl_absorpt_correction_T_min  0.6084
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.445
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.032(15)
_refine_ls_extinction_coef       0.0386(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     650
_refine_ls_number_reflns         7419
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0803P)²+0.1540P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                6654
_reflns_number_total             7419
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1544.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2012770
_cod_database_fobs_code          2012770
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Br1 1.31391(4) 0.70497(3) 0.08320(8) 0.1492(3) Uani d . 1 . . Br
N1 0.6620(2) 0.53291(11) 0.2724(2) 0.0698(5) Uani d . 1 . . N
C2 0.6512(3) 0.46973(14) 0.3022(3) 0.0754(7) Uani d . 1 . . C
H2A 0.6698 0.4457 0.2351 0.090 Uiso calc R 1 . . H
H2B 0.5673 0.4613 0.3223 0.090 Uiso calc R 1 . . H
C3 0.7381(3) 0.45283(14) 0.4034(3) 0.0733(7) Uani d . 1 . . C
H3A 0.7203 0.4114 0.4237 0.088 Uiso calc R 1 . . H
C4 0.7076(3) 0.49106(13) 0.5071(2) 0.0696(6) Uani d . 1 . . C
H4A 0.6219 0.4823 0.5241 0.083 Uiso calc R 1 . . H
C5 0.7123(4) 0.55663(14) 0.4767(3) 0.0832(8) Uani d . 1 . . C
H5A 0.7960 0.5679 0.4604 0.100 Uiso calc R 1 . . H
H5B 0.6862 0.5802 0.5418 0.100 Uiso calc R 1 . . H
C6 0.6281(4) 0.56853(16) 0.3709(3) 0.0856(9) Uani d . 1 . . C
H6A 0.5439 0.5596 0.3896 0.103 Uiso calc R 1 . . H
H6B 0.6324 0.6104 0.3507 0.103 Uiso calc R 1 . . H
N7 0.7828(2) 0.47563(11) 0.6141(2) 0.0719(6) Uani d . 1 . . N
C8 0.7520(3) 0.42505(14) 0.6712(3) 0.0760(7) Uani d . 1 . . C
O8 0.6656(2) 0.39404(11) 0.6390(2) 0.0890(6) Uani d . 1 . . O
C9 0.8341(4) 0.40870(17) 0.7771(3) 0.0928(10) Uani d . 1 . . C
H9A 0.9170 0.4013 0.7524 0.111 Uiso calc R 1 . . H
H9B 0.8373 0.4420 0.8306 0.111 Uiso calc R 1 . . H
C10 0.7883(5) 0.3544(2) 0.8388(4) 0.1120(13) Uani d . 1 . . C
H10A 0.8422 0.3457 0.9045 0.168 Uiso calc R 1 . . H
H10B 0.7865 0.3211 0.7866 0.168 Uiso calc R 1 . . H
H10C 0.7069 0.3618 0.8647 0.168 Uiso calc R 1 . . H
C1A 0.8760(3) 0.51521(15) 0.6590(3) 0.0808(8) Uani d . 1 . . C
C6A 0.8415(5) 0.56342(17) 0.7281(3) 0.0957(11) Uani d . 1 . . C
H6AA 0.7594 0.5694 0.7444 0.115 Uiso calc R 1 . . H
C5A 0.9312(8) 0.6020(2) 0.7715(4) 0.131(2) Uani d . 1 . . C
H5AA 0.9093 0.6348 0.8152 0.157 Uiso calc R 1 . . H
C4A 1.0528(8) 0.5916(3) 0.7498(6) 0.148(3) Uani d . 1 . . C
H4AA 1.1130 0.6175 0.7793 0.177 Uiso calc R 1 . . H
C3A 1.0859(6) 0.5439(3) 0.6855(6) 0.142(2) Uani d . 1 . . C
H3AA 1.1688 0.5372 0.6732 0.170 Uiso calc R 1 . . H
C2A 0.9984(4) 0.5050(2) 0.6379(4) 0.1019(11) Uani d . 1 . . C
H2AA 1.0217 0.4729 0.5928 0.122 Uiso calc R 1 . . H
C1' 0.5864(3) 0.54758(16) 0.1685(3) 0.0750(7) Uani d . 1 . . C
H1'A 0.5699 0.5900 0.1675 0.090 Uiso calc R 1 . . H
H1'B 0.5082 0.5270 0.1716 0.090 Uiso calc R 1 . . H
C2' 0.6476(3) 0.53051(14) 0.0583(2) 0.0703(7) Uani d . 1 . . C
H2'A 0.6703 0.4883 0.0623 0.084 Uiso calc R 1 . . H
C1B 0.5714(3) 0.54131(14) -0.0503(2) 0.0708(7) Uani d . 1 . . C
C6B 0.5606(4) 0.49751(19) -0.1339(3) 0.0934(9) Uani d . 1 . . C
H6BA 0.6003 0.4613 -0.1214 0.112 Uiso calc R 1 . . H
C5B 0.4918(4) 0.5063(2) -0.2364(4) 0.1066(13) Uani d . 1 . . C
H5BA 0.4868 0.4765 -0.2924 0.128 Uiso calc R 1 . . H
C4B 0.4314(4) 0.5591(3) -0.2544(4) 0.1085(14) Uani d . 1 . . C
H4BA 0.3856 0.5654 -0.3231 0.130 Uiso calc R 1 . . H
C3B 0.4383(4) 0.6027(2) -0.1714(4) 0.1123(14) Uani d . 1 . . C
H3BA 0.3946 0.6379 -0.1826 0.135 Uiso calc R 1 . . H
C2B 0.5105(4) 0.59443(19) -0.0703(3) 0.0940(10) Uani d . 1 . . C
H2BA 0.5177 0.6249 -0.0158 0.113 Uiso calc R 1 . . H
O11 0.75949(19) 0.56638(9) 0.05400(19) 0.0746(5) Uani d . 1 . . O
C12X 0.8672(3) 0.53824(14) 0.0593(3) 0.0737(7) Uani d . 1 . . C
O12 0.8776(2) 0.48459(11) 0.0566(3) 0.0994(7) Uani d . 1 . . O
C1C 0.9738(3) 0.57982(14) 0.0691(3) 0.0714(7) Uani d . 1 . . C
C6C 0.9585(3) 0.64092(18) 0.0714(3) 0.0909(9) Uani d . 1 . . C
H6CA 0.8796 0.6570 0.0709 0.109 Uiso calc R 1 . . H
C5C 1.0593(4) 0.67826(19) 0.0746(5) 0.1072(13) Uani d . 1 . . C
H5CA 1.0495 0.7194 0.0736 0.129 Uiso calc R 1 . . H
C4C 1.1755(3) 0.65304(19) 0.0794(4) 0.0977(11) Uani d . 1 . . C
C3C 1.1926(3) 0.59317(19) 0.0764(4) 0.0977(10) Uani d . 1 . . C
H3CA 1.2715 0.5772 0.0775 0.117 Uiso calc R 1 . . H
C2C 1.0909(3) 0.55651(18) 0.0714(3) 0.0902(9) Uani d . 1 . . C
H2CA 1.1015 0.5155 0.0697 0.108 Uiso calc R 1 . . H
C3' 0.8706(4) 0.4553(2) 0.3692(3) 0.0980(11) Uani d . 1 . . C
H3'A 0.9233 0.4445 0.4345 0.147 Uiso calc R 1 . . H
H3'B 0.8900 0.4950 0.3449 0.147 Uiso calc R 1 . . H
H3'C 0.8828 0.4281 0.3065 0.147 Uiso calc R 1 . . H
N11 0.3408(2) 0.30120(12) 0.8114(2) 0.0780(6) Uani d . 1 . . N
Br11 -0.34520(5) 0.14363(3) 0.57529(8) 0.1575(3) Uani d . 1 . . Br
C12 0.3757(4) 0.36120(19) 0.8462(3) 0.0946(10) Uani d . 1 . . C
H12A 0.3732 0.3869 0.7786 0.114 Uiso calc R 1 . . H
H12B 0.4593 0.3609 0.8785 0.114 Uiso calc R 1 . . H
C13 0.2903(4) 0.38568(16) 0.9356(3) 0.0877(9) Uani d . 1 . . C
H13A 0.3238 0.4242 0.9613 0.105 Uiso calc R 1 . . H
C14 0.2958(3) 0.34423(16) 1.0410(3) 0.0763(7) Uani d . 1 . . C
H14A 0.3813 0.3443 1.0709 0.092 Uiso calc R 1 . . H
C15 0.2663(3) 0.28030(15) 1.0042(3) 0.0835(8) Uani d . 1 . . C
H15A 0.2770 0.2540 1.0705 0.100 Uiso calc R 1 . . H
H15B 0.1813 0.2777 0.9760 0.100 Uiso calc R 1 . . H
C16 0.3508(3) 0.26102(18) 0.9093(3) 0.0874(9) Uani d . 1 . . C
H16A 0.4351 0.2604 0.9397 0.105 Uiso calc R 1 . . H
H16B 0.3291 0.2211 0.8840 0.105 Uiso calc R 1 . . H
N17 0.2197(2) 0.36480(12) 1.1372(2) 0.0737(6) Uani d . 1 . . N
C18 0.2643(3) 0.41108(18) 1.2029(3) 0.0845(8) Uani d . 1 . . C
O18 0.3590(2) 0.43685(15) 1.1791(2) 0.1107(9) Uani d . 1 . . O
C19 0.1906(4) 0.4295(2) 1.3054(4) 0.0988(11) Uani d . 1 . . C
H19A 0.1094 0.4420 1.2776 0.119 Uiso calc R 1 . . H
H19B 0.1806 0.3953 1.3556 0.119 Uiso calc R 1 . . H
C20 0.2490(6) 0.4787(3) 1.3742(6) 0.148(3) Uani d . 1 . . C
H20A 0.1985 0.4886 1.4379 0.223 Uiso calc R 1 . . H
H20B 0.2575 0.5130 1.3255 0.223 Uiso calc R 1 . . H
H20C 0.3287 0.4663 1.4035 0.223 Uiso calc R 1 . . H
C11A 0.1114(3) 0.33283(14) 1.1701(2) 0.0707(7) Uani d . 1 . . C
C12A 0.1226(4) 0.28576(18) 1.2477(3) 0.0918(10) Uani d . 1 . . C
H12C 0.1995 0.2745 1.2781 0.110 Uiso calc R 1 . . H
C13A 0.0174(6) 0.25561(19) 1.2794(4) 0.1134(15) Uani d . 1 . . C
H13B 0.0240 0.2235 1.3301 0.136 Uiso calc R 1 . . H
C14A -0.0949(5) 0.2729(3) 1.2367(4) 0.1196(16) Uani d . 1 . . C
H14B -0.1647 0.2528 1.2595 0.143 Uiso calc R 1 . . H
C15A -0.1070(4) 0.3191(3) 1.1611(4) 0.1117(14) Uani d . 1 . . C
H15C -0.1844 0.3303 1.1317 0.134 Uiso calc R 1 . . H
C16A -0.0040(3) 0.34938(18) 1.1285(3) 0.0869(8) Uani d . 1 . . C
H16C -0.0123 0.3814 1.0777 0.104 Uiso calc R 1 . . H
C11' 0.4041(3) 0.28139(17) 0.7090(3) 0.0802(8) Uani d . 1 . . C
H11A 0.4110 0.2383 0.7098 0.096 Uiso calc R 1 . . H
H11B 0.4865 0.2979 0.7104 0.096 Uiso calc R 1 . . H
C12' 0.3342(3) 0.30112(16) 0.5995(3) 0.0778(7) Uani d . 1 . . C
H12D 0.3202 0.3442 0.6021 0.093 Uiso calc R 1 . . H
C11B 0.3966(3) 0.28517(14) 0.4889(3) 0.0743(7) Uani d . 1 . . C
C16B 0.4690(4) 0.32519(19) 0.4352(3) 0.0980(11) Uani d . 1 . . C
H1CA 0.4820 0.3625 0.4685 0.118 Uiso calc R 1 . . H
C15B 0.5236(5) 0.3117(2) 0.3325(4) 0.1121(13) Uani d . 1 . . C
H15D 0.5720 0.3399 0.2969 0.135 Uiso calc R 1 . . H
C14B 0.5067(4) 0.2573(2) 0.2833(3) 0.1044(12) Uani d . 1 . . C
H14C 0.5443 0.2480 0.2146 0.125 Uiso calc R 1 . . H
C13B 0.4333(5) 0.2159(2) 0.3356(4) 0.1095(12) Uani d . 1 . . C
H13C 0.4200 0.1788 0.3014 0.131 Uiso calc R 1 . . H
C12B 0.3797(4) 0.22966(17) 0.4394(4) 0.0973(10) Uani d . 1 . . C
H12E 0.3322 0.2014 0.4759 0.117 Uiso calc R 1 . . H
O21 0.21741(19) 0.27019(11) 0.5997(2) 0.0810(5) Uani d . 1 . . O
C22 0.1136(3) 0.30167(15) 0.5851(2) 0.0734(7) Uani d . 1 . . C
O22 0.1111(3) 0.35448(13) 0.5727(3) 0.1037(7) Uani d . 1 . . O
C11C 0.0040(3) 0.26211(15) 0.5863(2) 0.0714(7) Uani d . 1 . . C
C16C -0.1106(3) 0.28650(18) 0.5620(3) 0.0918(9) Uani d . 1 . . C
H16D -0.1178 0.3271 0.5479 0.110 Uiso calc R 1 . . H
C15C -0.2147(4) 0.2513(2) 0.5585(4) 0.0977(10) Uani d . 1 . . C
H15E -0.2918 0.2676 0.5415 0.117 Uiso calc R 1 . . H
C14C -0.2014(3) 0.1925(2) 0.5803(4) 0.0990(11) Uani d . 1 . . C
C13C -0.0908(4) 0.1661(2) 0.6040(5) 0.1201(15) Uani d . 1 . . C
H13D -0.0851 0.1253 0.6173 0.144 Uiso calc R 1 . . H
C12C 0.0137(3) 0.20201(19) 0.6078(4) 0.0959(10) Uani d . 1 . . C
H12F 0.0904 0.1853 0.6250 0.115 Uiso calc R 1 . . H
C13' 0.1613(5) 0.3970(2) 0.8846(3) 0.1101(13) Uani d . 1 . . C
H13E 0.1658 0.4233 0.8192 0.165 Uiso calc R 1 . . H
H13F 0.1120 0.4150 0.9423 0.165 Uiso calc R 1 . . H
H13G 0.1249 0.3600 0.8600 0.165 Uiso calc R 1 . . H
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'
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'
Br Br -0.6763 1.2805 '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_publ_flag
C6 N1 C1' 111.4(2) yes
C6 N1 C2 109.0(2) yes
C1' N1 C2 111.2(2) yes
N1 C2 C3 111.6(2) ?
N1 C2 H2A 109.3 ?
C3 C2 H2A 109.3 ?
N1 C2 H2B 109.3 ?
C3 C2 H2B 109.3 ?
H2A C2 H2B 108.0 ?
C3' C3 C4 115.1(3) ?
C3' C3 C2 111.2(3) ?
C4 C3 C2 108.3(2) ?
C3' C3 H3A 107.3 ?
C4 C3 H3A 107.3 ?
C2 C3 H3A 107.3 ?
N7 C4 C5 113.2(2) ?
N7 C4 C3 112.9(2) ?
C5 C4 C3 110.9(2) ?
N7 C4 H4A 106.4 ?
C5 C4 H4A 106.4 ?
C3 C4 H4A 106.4 ?
C4 C5 C6 109.4(3) ?
C4 C5 H5A 109.8 ?
C6 C5 H5A 109.8 ?
C4 C5 H5B 109.8 ?
C6 C5 H5B 109.8 ?
H5A C5 H5B 108.3 ?
N1 C6 C5 111.6(3) ?
N1 C6 H6A 109.3 ?
C5 C6 H6A 109.3 ?
N1 C6 H6B 109.3 ?
C5 C6 H6B 109.3 ?
H6A C6 H6B 108.0 ?
C8 N7 C1A 121.8(2) yes
C8 N7 C4 117.1(2) yes
C1A N7 C4 120.8(2) yes
O8 C8 N7 122.1(3) ?
O8 C8 C9 121.8(3) ?
N7 C8 C9 116.1(3) ?
C10 C9 C8 112.2(3) ?
C10 C9 H9A 109.2 ?
C8 C9 H9A 109.2 ?
C10 C9 H9B 109.2 ?
C8 C9 H9B 109.2 ?
H9A C9 H9B 107.9 ?
C9 C10 H10A 109.5 ?
C9 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
C9 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
C2A C1A C6A 120.5(3) ?
C2A C1A N7 120.5(3) ?
C6A C1A N7 118.9(3) ?
C5A C6A C1A 119.2(5) ?
C5A C6A H6AA 120.4 ?
C1A C6A H6AA 120.4 ?
C4A C5A C6A 119.8(6) ?
C4A C5A H5AA 120.1 ?
C6A C5A H5AA 120.1 ?
C3A C4A C5A 120.6(5) ?
C3A C4A H4AA 119.7 ?
C5A C4A H4AA 119.7 ?
C4A C3A C2A 121.3(6) ?
C4A C3A H3AA 119.4 ?
C2A C3A H3AA 119.4 ?
C1A C2A C3A 118.4(5) ?
C1A C2A H2AA 120.8 ?
C3A C2A H2AA 120.8 ?
N1 C1' C2' 112.3(2) ?
N1 C1' H1'A 109.1 ?
C2' C1' H1'A 109.1 ?
N1 C1' H1'B 109.1 ?
C2' C1' H1'B 109.1 ?
H1'A C1' H1'B 107.9 ?
O11 C2' C1B 108.5(2) ?
O11 C2' C1' 106.5(2) ?
C1B C2' C1' 114.6(2) ?
O11 C2' H2'A 109.0 ?
C1B C2' H2'A 109.0 ?
C1' C2' H2'A 109.0 ?
C6B C1B C2B 118.2(3) ?
C6B C1B C2' 120.0(3) ?
C2B C1B C2' 121.8(3) ?
C1B C6B C5B 121.4(4) ?
C1B C6B H6BA 119.3 ?
C5B C6B H6BA 119.3 ?
C4B C5B C6B 119.5(4) ?
C4B C5B H5BA 120.2 ?
C6B C5B H5BA 120.2 ?
C5B C4B C3B 120.1(4) ?
C5B C4B H4BA 120.0 ?
C3B C4B H4BA 120.0 ?
C4B C3B C2B 120.2(4) ?
C4B C3B H3BA 119.9 ?
C2B C3B H3BA 119.9 ?
C1B C2B C3B 120.4(4) ?
C1B C2B H2BA 119.8 ?
C3B C2B H2BA 119.8 ?
C12X O11 C2' 118.0(2) ?
O12 C12X O11 123.6(3) ?
O12 C12X C1C 123.6(3) ?
O11 C12X C1C 112.8(3) ?
C2C C1C C6C 119.3(3) ?
C2C C1C C12X 118.7(3) ?
C6C C1C C12X 122.0(3) ?
C5C C6C C1C 120.4(3) ?
C5C C6C H6CA 119.8 ?
C1C C6C H6CA 119.8 ?
C6C C5C C4C 118.4(4) ?
C6C C5C H5CA 120.8 ?
C4C C5C H5CA 120.8 ?
C3C C4C C5C 122.0(3) ?
C3C C4C Br1 119.9(3) ?
C5C C4C Br1 118.0(3) ?
C4C C3C C2C 118.8(3) ?
C4C C3C H3CA 120.6 ?
C2C C3C H3CA 120.6 ?
C1C C2C C3C 120.9(4) ?
C1C C2C H2CA 119.5 ?
C3C C2C H2CA 119.5 ?
C3 C3' H3'A 109.5 ?
C3 C3' H3'B 109.5 ?
H3'A C3' H3'B 109.5 ?
C3 C3' H3'C 109.5 ?
H3'A C3' H3'C 109.5 ?
H3'B C3' H3'C 109.5 ?
C16 N11 C12 110.6(3) yes
C16 N11 C11' 114.7(3) yes
C12 N11 C11' 112.3(3) yes
N11 C12 C13 111.3(3) ?
N11 C12 H12A 109.4 ?
C13 C12 H12A 109.4 ?
N11 C12 H12B 109.4 ?
C13 C12 H12B 109.4 ?
H12A C12 H12B 108.0 ?
C12 C13 C13' 112.2(3) ?
C12 C13 C14 108.2(3) ?
C13' C13 C14 114.6(3) ?
C12 C13 H13A 107.2 ?
C13' C13 H13A 107.2 ?
C14 C13 H13A 107.2 ?
N17 C14 C15 112.5(3) ?
N17 C14 C13 113.5(3) ?
C15 C14 C13 110.5(3) ?
N17 C14 H14A 106.6 ?
C15 C14 H14A 106.6 ?
C13 C14 H14A 106.6 ?
C16 C15 C14 110.0(3) ?
C16 C15 H15A 109.7 ?
C14 C15 H15A 109.7 ?
C16 C15 H15B 109.7 ?
C14 C15 H15B 109.7 ?
H15A C15 H15B 108.2 ?
N11 C16 C15 110.8(3) ?
N11 C16 H16A 109.5 ?
C15 C16 H16A 109.5 ?
N11 C16 H16B 109.5 ?
C15 C16 H16B 109.5 ?
H16A C16 H16B 108.1 ?
C18 N17 C11A 120.7(2) yes
C18 N17 C14 117.1(3) yes
C11A N17 C14 121.7(2) yes
O18 C18 N17 121.4(3) ?
O18 C18 C19 121.5(3) ?
N17 C18 C19 117.1(3) ?
C20 C19 C18 113.1(3) ?
C20 C19 H19A 109.0 ?
C18 C19 H19A 109.0 ?
C20 C19 H19B 109.0 ?
C18 C19 H19B 109.0 ?
H19A C19 H19B 107.8 ?
C19 C20 H20A 109.5 ?
C19 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C19 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C16A C11A C12A 119.2(3) ?
C16A C11A N17 121.1(3) ?
C12A C11A N17 119.7(3) ?
C11A C12A C13A 119.2(4) ?
C11A C12A H12C 120.4 ?
C13A C12A H12C 120.4 ?
C14A C13A C12A 120.3(4) ?
C14A C13A H13B 119.9 ?
C12A C13A H13B 119.9 ?
C13A C14A C15A 121.0(4) ?
C13A C14A H14B 119.5 ?
C15A C14A H14B 119.5 ?
C14A C15A C16A 119.5(5) ?
C14A C15A H15C 120.2 ?
C16A C15A H15C 120.2 ?
C15A C16A C11A 120.8(4) ?
C15A C16A H16C 119.6 ?
C11A C16A H16C 119.6 ?
N11 C11' C12' 110.3(3) ?
N11 C11' H11A 109.6 ?
C12' C11' H11A 109.6 ?
N11 C11' H11B 109.6 ?
C12' C11' H11B 109.6 ?
H11A C11' H11B 108.1 ?
O21 C12' C11B 108.1(3) ?
O21 C12' C11' 105.7(3) ?
C11B C12' C11' 114.0(3) ?
O21 C12' H12D 109.6 ?
C11B C12' H12D 109.6 ?
C11' C12' H12D 109.6 ?
C16B C11B C12B 118.6(3) ?
C16B C11B C12' 121.0(3) ?
C12B C11B C12' 120.4(3) ?
C11B C16B C15B 121.5(4) ?
C11B C16B H1CA 119.3 ?
C15B C16B H1CA 119.3 ?
C14B C15B C16B 120.1(4) ?
C14B C15B H15D 120.0 ?
C16B C15B H15D 120.0 ?
C15B C14B C13B 119.8(4) ?
C15B C14B H14C 120.1 ?
C13B C14B H14C 120.1 ?
C14B C13B C12B 119.7(4) ?
C14B C13B H13C 120.2 ?
C12B C13B H13C 120.2 ?
C11B C12B C13B 120.4(4) ?
C11B C12B H12E 119.8 ?
C13B C12B H12E 119.8 ?
C22 O21 C12' 118.9(3) ?
O22 C22 O21 123.7(3) ?
O22 C22 C11C 125.5(3) ?
O21 C22 C11C 110.9(3) ?
C12C C11C C16C 119.2(3) ?
C12C C11C C22 122.2(3) ?
C16C C11C C22 118.6(3) ?
C15C C16C C11C 120.8(4) ?
C15C C16C H16D 119.6 ?
C11C C16C H16D 119.6 ?
C14C C15C C16C 118.2(4) ?
C14C C15C H15E 120.9 ?
C16C C15C H15E 120.9 ?
C15C C14C C13C 123.4(4) ?
C15C C14C Br11 118.3(3) ?
C13C C14C Br11 118.3(4) ?
C14C C13C C12C 118.0(4) ?
C14C C13C H13D 121.0 ?
C12C C13C H13D 121.0 ?
C11C C12C C13C 120.4(4) ?
C11C C12C H12F 119.8 ?
C13C C12C H12F 119.8 ?
C13 C13' H13E 109.5 ?
C13 C13' H13F 109.5 ?
H13E C13' H13F 109.5 ?
C13 C13' H13G 109.5 ?
H13E C13' H13G 109.5 ?
H13F C13' H13G 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C4C . 1.904(4) yes
N1 C6 . 1.449(4) yes
N1 C1' . 1.465(4) yes
N1 C2 . 1.466(4) yes
C2 C3 . 1.522(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C3' . 1.510(5) ?
C3 C4 . 1.520(4) ?
C3 H3A . 0.9800 ?
C4 N7 . 1.494(3) yes
C4 C5 . 1.515(4) ?
C4 H4A . 0.9800 ?
C5 C6 . 1.521(5) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
N7 C8 . 1.362(4) yes
N7 C1A . 1.431(4) yes
C8 O8 . 1.217(4) ?
C8 C9 . 1.530(4) ?
C9 C10 . 1.507(6) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C1A C2A . 1.382(6) ?
C1A C6A . 1.404(6) ?
C6A C5A . 1.384(7) ?
C6A H6AA . 0.9300 ?
C5A C4A . 1.376(10) ?
C5A H5AA . 0.9300 ?
C4A C3A . 1.359(11) ?
C4A H4AA . 0.9300 ?
C3A C2A . 1.390(7) ?
C3A H3AA . 0.9300 ?
C2A H2AA . 0.9300 ?
C1' C2' . 1.506(4) ?
C1' H1'A . 0.9700 ?
C1' H1'B . 0.9700 ?
C2' O11 . 1.463(4) ?
C2' C1B . 1.495(4) ?
C2' H2'A . 0.9800 ?
C1B C6B . 1.379(5) ?
C1B C2B . 1.380(5) ?
C6B C5B . 1.389(6) ?
C6B H6BA . 0.9300 ?
C5B C4B . 1.368(7) ?
C5B H5BA . 0.9300 ?
C4B C3B . 1.369(8) ?
C4B H4BA . 0.9300 ?
C3B C2B . 1.394(6) ?
C3B H3BA . 0.9300 ?
C2B H2BA . 0.9300 ?
O11 C12X . 1.331(4) ?
C12X O12 . 1.211(4) ?
C12X C1C . 1.490(4) ?
C1C C2C . 1.376(5) ?
C1C C6C . 1.383(5) ?
C6C C5C . 1.381(6) ?
C6C H6CA . 0.9300 ?
C5C C4C . 1.385(6) ?
C5C H5CA . 0.9300 ?
C4C C3C . 1.358(6) ?
C3C C2C . 1.379(6) ?
C3C H3CA . 0.9300 ?
C2C H2CA . 0.9300 ?
C3' H3'A . 0.9600 ?
C3' H3'B . 0.9600 ?
C3' H3'C . 0.9600 ?
N11 C16 . 1.446(5) yes
N11 C12 . 1.453(5) yes
N11 C11' . 1.459(4) yes
Br11 C14C . 1.910(4) yes
C12 C13 . 1.518(5) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C13' . 1.522(6) ?
C13 C14 . 1.530(5) ?
C13 H13A . 0.9800 ?
C14 N17 . 1.483(4) yes
C14 C15 . 1.528(5) ?
C14 H14A . 0.9800 ?
C15 C16 . 1.520(5) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
N17 C18 . 1.364(4) yes
N17 C11A . 1.444(4) yes
C18 O18 . 1.222(4) ?
C18 C19 . 1.511(5) ?
C19 C20 . 1.489(6) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C11A C16A . 1.377(5) ?
C11A C12A . 1.388(5) ?
C12A C13A . 1.392(7) ?
C12A H12C . 0.9300 ?
C13A C14A . 1.356(8) ?
C13A H13B . 0.9300 ?
C14A C15A . 1.359(8) ?
C14A H14B . 0.9300 ?
C15A C16A . 1.376(6) ?
C15A H15C . 0.9300 ?
C16A H16C . 0.9300 ?
C11' C12' . 1.516(5) ?
C11' H11A . 0.9700 ?
C11' H11B . 0.9700 ?
C12' O21 . 1.448(4) ?
C12' C11B . 1.510(4) ?
C12' H12D . 0.9800 ?
C11B C16B . 1.361(5) ?
C11B C12B . 1.381(5) ?
C16B C15B . 1.378(6) ?
C16B H1CA . 0.9300 ?
C15B C14B . 1.356(7) ?
C15B H15D . 0.9300 ?
C14B C13B . 1.381(7) ?
C14B H14C . 0.9300 ?
C13B C12B . 1.386(6) ?
C13B H13C . 0.9300 ?
C12B H12E . 0.9300 ?
O21 C22 . 1.338(4) ?
C22 O22 . 1.195(4) ?
C22 C11C . 1.488(5) ?
C11C C12C . 1.376(5) ?
C11C C16C . 1.381(5) ?
C16C C15C . 1.380(6) ?
C16C H16D . 0.9300 ?
C15C C14C . 1.352(7) ?
C15C H15E . 0.9300 ?
C14C C13C . 1.359(6) ?
C13C C12C . 1.393(6) ?
C13C H13D . 0.9300 ?
C12C H12F . 0.9300 ?
C13' H13E . 0.9600 ?
C13' H13F . 0.9600 ?
C13' H13G . 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
C6 N1 C2 C3 -61.9(3)
C1' N1 C2 C3 174.9(3)
N1 C2 C3 C3' -68.6(4)
N1 C2 C3 C4 58.8(3)
C3' C3 C4 N7 -58.3(4)
C2 C3 C4 N7 176.6(3)
C3' C3 C4 C5 70.0(4)
C2 C3 C4 C5 -55.2(3)
N7 C4 C5 C6 -177.0(3)
C3 C4 C5 C6 54.9(4)
C1' N1 C6 C5 -175.9(3)
C2 N1 C6 C5 60.9(4)
C4 C5 C6 N1 -57.9(4)
C5 C4 N7 C8 157.3(3)
C3 C4 N7 C8 -75.6(3)
C5 C4 N7 C1A -17.7(4)
C3 C4 N7 C1A 109.4(3)
C1A N7 C8 O8 173.3(3)
C4 N7 C8 O8 -1.6(5)
C1A N7 C8 C9 -8.0(5)
C4 N7 C8 C9 177.2(3)
O8 C8 C9 C10 -4.8(6)
N7 C8 C9 C10 176.4(4)
C8 N7 C1A C2A 85.0(4)
C4 N7 C1A C2A -100.3(4)
C8 N7 C1A C6A -93.0(4)
C4 N7 C1A C6A 81.7(4)
C2A C1A C6A C5A 2.3(5)
N7 C1A C6A C5A -179.8(3)
C1A C6A C5A C4A -2.1(7)
C6A C5A C4A C3A 0.3(8)
C5A C4A C3A C2A 1.4(9)
C6A C1A C2A C3A -0.6(6)
N7 C1A C2A C3A -178.6(4)
C4A C3A C2A C1A -1.2(8)
C6 N1 C1' C2' 157.8(3)
C2 N1 C1' C2' -80.4(3)
N1 C1' C2' O11 -63.3(3)
N1 C1' C2' C1B 176.7(2)
O11 C2' C1B C6B 108.4(3)
C1' C2' C1B C6B -132.7(3)
O11 C2' C1B C2B -71.6(4)
C1' C2' C1B C2B 47.3(4)
C2B C1B C6B C5B 0.8(5)
C2' C1B C6B C5B -179.2(3)
C1B C6B C5B C4B -1.2(6)
C6B C5B C4B C3B -0.5(6)
C5B C4B C3B C2B 2.5(7)
C6B C1B C2B C3B 1.3(6)
C2' C1B C2B C3B -178.7(3)
C4B C3B C2B C1B -2.9(6)
C1B C2' O11 C12X -120.5(3)
C1' C2' O11 C12X 115.6(3)
C2' O11 C12X O12 7.2(4)
C2' O11 C12X C1C -172.8(2)
O12 C12X C1C C2C 2.2(5)
O11 C12X C1C C2C -177.9(3)
O12 C12X C1C C6C 179.7(4)
O11 C12X C1C C6C -0.3(4)
C2C C1C C6C C5C 0.8(6)
C12X C1C C6C C5C -176.7(4)
C1C C6C C5C C4C -2.2(7)
C6C C5C C4C C3C 2.7(7)
C6C C5C C4C Br1 179.8(3)
C5C C4C C3C C2C -1.8(7)
Br1 C4C C3C C2C -178.8(3)
C6C C1C C2C C3C 0.1(6)
C12X C1C C2C C3C 177.7(3)
C4C C3C C2C C1C 0.3(6)
C16 N11 C12 C13 -62.5(4)
C11' N11 C12 C13 168.0(3)
N11 C12 C13 C13' -68.5(5)
N11 C12 C13 C14 58.9(4)
C12 C13 C14 N17 177.6(3)
C13' C13 C14 N17 -56.4(4)
C12 C13 C14 C15 -54.9(4)
C13' C13 C14 C15 71.1(4)
N17 C14 C15 C16 -177.5(3)
C13 C14 C15 C16 54.4(4)
C12 N11 C16 C15 60.6(4)
C11' N11 C16 C15 -171.1(3)
C14 C15 C16 N11 -56.7(4)
C15 C14 N17 C18 157.9(3)
C13 C14 N17 C18 -75.6(4)
C15 C14 N17 C11A -14.3(4)
C13 C14 N17 C11A 112.2(3)
C11A N17 C18 O18 176.7(4)
C14 N17 C18 O18 4.4(5)
C11A N17 C18 C19 -4.0(5)
C14 N17 C18 C19 -176.3(3)
O18 C18 C19 C20 -2.9(7)
N17 C18 C19 C20 177.8(5)
C18 N17 C11A C16A 91.9(4)
C14 N17 C11A C16A -96.2(4)
C18 N17 C11A C12A -86.1(4)
C14 N17 C11A C12A 85.8(4)
C16A C11A C12A C13A 1.4(5)
N17 C11A C12A C13A 179.5(3)
C11A C12A C13A C14A -1.3(6)
C12A C13A C14A C15A 1.0(7)
C13A C14A C15A C16A -0.8(7)
C14A C15A C16A C11A 0.9(6)
C12A C11A C16A C15A -1.3(5)
N17 C11A C16A C15A -179.3(3)
C16 N11 C11' C12' 146.2(3)
C12 N11 C11' C12' -86.4(4)
N11 C11' C12' O21 -64.3(3)
N11 C11' C12' C11B 177.1(3)
O21 C12' C11B C16B 146.8(3)
C11' C12' C11B C16B -96.0(4)
O21 C12' C11B C12B -32.3(4)
C11' C12' C11B C12B 84.8(4)
C12B C11B C16B C15B 1.0(7)
C12' C11B C16B C15B -178.1(4)
C11B C16B C15B C14B -0.7(8)
C16B C15B C14B C13B 0.9(8)
C15B C14B C13B C12B -1.4(8)
C16B C11B C12B C13B -1.6(6)
C12' C11B C12B C13B 177.6(4)
C14B C13B C12B C11B 1.8(7)
C11B C12' O21 C22 -109.2(3)
C11' C12' O21 C22 128.4(3)
C12' O21 C22 O22 -0.7(4)
C12' O21 C22 C11C 179.2(2)
O22 C22 C11C C12C -176.1(4)
O21 C22 C11C C12C 3.9(4)
O22 C22 C11C C16C 5.6(5)
O21 C22 C11C C16C -174.3(3)
C12C C11C C16C C15C -0.4(5)
C22 C11C C16C C15C 177.9(3)
C11C C16C C15C C14C 0.6(6)
C16C C15C C14C C13C -1.0(7)
C16C C15C C14C Br11 -179.9(3)
C15C C14C C13C C12C 1.2(8)
Br11 C14C C13C C12C -179.9(4)
C16C C11C C12C C13C 0.6(6)
C22 C11C C12C C13C -177.6(4)
C14C C13C C12C C11C -1.0(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24724557
