#------------------------------------------------------------------------------
#$Date: 2017-07-25 12:23:32 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199108 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/21/2242130.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_2242130
loop_
_publ_author_name
'Stephenson, Clifton J.'
'Mague, Joel T.'
'Kamm, Nathaniel'
'Aleman, Nathalie'
'Rich, Dayla'
'Dang, Quynh-Nhu'
'Nguyen, Ha Van'
_publ_section_title
;
 Synthesis, resolution and crystal structures of two enantiomeric
 rhodamine derivatives
;
_journal_coeditor_code           SJ5518
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              327
_journal_page_last               333
_journal_paper_doi               10.1107/S2056989017001451
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C24 H20 Br N O3'
_chemical_formula_moiety         'C24 H20 Br N O3'
_chemical_formula_sum            'C24 H20 Br N O3'
_chemical_formula_weight         450.32
_chemical_name_systematic
(1R)-6'-Bromo-3'-diethylamino-3H-spiro[2-benzofuran-1,9'-xanthen]-3-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.1529(13)
_cell_length_b                   18.185(3)
_cell_length_c                   26.860(4)
_cell_measurement_reflns_used    7498
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.2964
_cell_measurement_theta_min      2.2399
_cell_volume                     3982.3(11)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            38240
_diffrn_reflns_theta_full        28.500
_diffrn_reflns_theta_max         29.139
_diffrn_reflns_theta_min         1.352
_exptl_absorpt_coefficient_mu    2.090
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.920
_refine_diff_density_min         -0.342
_refine_ls_abs_structure_details
;
Flack x determined using 2575 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   -0.002(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         10174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0445
_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)+(0.0089P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                7285
_reflns_number_total             10174
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sj5518sup1.cif
_cod_data_source_block           5
_cod_database_code               2242130
_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   0.612
_shelx_estimated_absorpt_t_max   0.921
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
Br Br1 0.52585(6) 0.63496(3) 0.28218(2) 0.02849(13) Uani d 1
O O1 0.6662(4) 0.57150(16) 0.46407(11) 0.0189(7) Uani d 1
O O2 0.4245(3) 0.39341(16) 0.46124(11) 0.0153(7) Uani d 1
O O3 0.2630(4) 0.29559(18) 0.44638(11) 0.0207(7) Uani d 1
N N1 0.8582(5) 0.5506(2) 0.63051(13) 0.0178(8) Uani d 1
C C1 0.6260(5) 0.5413(2) 0.41884(16) 0.0160(10) Uani d 1
C C2 0.6056(5) 0.5918(2) 0.38032(16) 0.0181(10) Uani d 1
H H2 0.6212 0.6429 0.3860 0.022 Uiso calc 1
C C3 0.5626(5) 0.5663(3) 0.33398(16) 0.0191(10) Uani d 1
C C4 0.5443(5) 0.4916(3) 0.32441(16) 0.0199(10) Uani d 1
H H4 0.5175 0.4747 0.2920 0.024 Uiso calc 1
C C5 0.5659(5) 0.4425(2) 0.36318(16) 0.0180(10) Uani d 1
H H5 0.5552 0.3913 0.3571 0.022 Uiso calc 1
C C6 0.6035(5) 0.4671(2) 0.41148(16) 0.0149(9) Uani d 1
C C7 0.6029(5) 0.4136(2) 0.45477(15) 0.0136(9) Uani d 1
C C8 0.6652(5) 0.4501(2) 0.50108(15) 0.0130(9) Uani d 1
C C9 0.6964(5) 0.4098(2) 0.54461(16) 0.0157(10) Uani d 1
H H9 0.6778 0.3583 0.5443 0.019 Uiso calc 1
C C10 0.7528(5) 0.4418(2) 0.58754(16) 0.0137(9) Uani d 1
H H10 0.7699 0.4124 0.6163 0.016 Uiso calc 1
C C11 0.7859(5) 0.5186(2) 0.58949(16) 0.0152(9) Uani d 1
C C12 0.7507(5) 0.5598(2) 0.54662(16) 0.0156(10) Uani d 1
H H12 0.7657 0.6116 0.5467 0.019 Uiso calc 1
C C13 0.6939(5) 0.5246(2) 0.50400(16) 0.0147(9) Uani d 1
C C14 0.8803(6) 0.5091(3) 0.67630(16) 0.0214(11) Uani d 1
H H14A 0.9644 0.5337 0.6970 0.026 Uiso calc 1
H H14B 0.9215 0.4594 0.6680 0.026 Uiso calc 1
C C15 0.7228(6) 0.5018(3) 0.70632(17) 0.0221(11) Uani d 1
H H15A 0.6887 0.5504 0.7182 0.033 Uiso calc 1
H H15B 0.7420 0.4693 0.7349 0.033 Uiso calc 1
H H15C 0.6365 0.4809 0.6852 0.033 Uiso calc 1
C C16 0.8935(5) 0.6297(3) 0.63138(17) 0.0219(10) Uani d 1
H H16A 0.9442 0.6437 0.5993 0.026 Uiso calc 1
H H16B 0.9746 0.6396 0.6580 0.026 Uiso calc 1
C C17 0.7432(6) 0.6778(3) 0.64011(19) 0.0303(13) Uani d 1
H H17A 0.7756 0.7297 0.6393 0.045 Uiso calc 1
H H17B 0.6955 0.6663 0.6727 0.045 Uiso calc 1
H H17C 0.6620 0.6684 0.6140 0.045 Uiso calc 1
C C18 0.6792(5) 0.3401(2) 0.44466(15) 0.0131(9) Uani d 1
C C19 0.8454(5) 0.3221(2) 0.44054(16) 0.0153(10) Uani d 1
H H19 0.9282 0.3586 0.4430 0.018 Uiso calc 1
C C20 0.8845(6) 0.2494(2) 0.43276(15) 0.0179(10) Uani d 1
H H20 0.9964 0.2357 0.4295 0.022 Uiso calc 1
C C21 0.7630(6) 0.1948(2) 0.42956(16) 0.0174(10) Uani d 1
H H21 0.7943 0.1451 0.4244 0.021 Uiso calc 1
C C22 0.5991(6) 0.2123(2) 0.43380(15) 0.0163(10) Uani d 1
H H22 0.5162 0.1757 0.4315 0.020 Uiso calc 1
C C23 0.5604(5) 0.2865(2) 0.44160(15) 0.0132(9) Uani d 1
C C24 0.3991(6) 0.3206(2) 0.44915(15) 0.0146(9) Uani d 1
Br Br2 0.41662(7) 0.36508(3) 0.88995(2) 0.03217(14) Uani d 1
O O4 0.3369(4) 0.51090(15) 0.72672(11) 0.0169(7) Uani d 1
O O5 0.2069(3) 0.69908(16) 0.79230(11) 0.0160(7) Uani d 1
O O6 0.1534(4) 0.80937(16) 0.82613(12) 0.0197(7) Uani d 1
N N2 0.2868(5) 0.61160(19) 0.56403(13) 0.0177(9) Uani d 1
C C25 0.3579(5) 0.5173(2) 0.77747(15) 0.0138(9) Uani d 1
C C26 0.3746(5) 0.4512(2) 0.80330(16) 0.0181(10) Uani d 1
H H26 0.3753 0.4054 0.7863 0.022 Uiso calc 1
C C27 0.3900(6) 0.4545(2) 0.85438(17) 0.0216(11) Uani d 1
C C28 0.3868(6) 0.5198(2) 0.88052(17) 0.0210(11) Uani d 1
H H28 0.3940 0.5202 0.9158 0.025 Uiso calc 1
C C29 0.3727(5) 0.5850(3) 0.85389(16) 0.0188(10) Uani d 1
H H29 0.3722 0.6305 0.8713 0.023 Uiso calc 1
C C30 0.3594(5) 0.5848(2) 0.80207(16) 0.0147(9) Uani d 1
C C31 0.3510(5) 0.6566(2) 0.77414(16) 0.0149(9) Uani d 1
C C32 0.3316(5) 0.6439(2) 0.71915(16) 0.0134(9) Uani d 1
C C33 0.3218(5) 0.7029(2) 0.68601(17) 0.0167(10) Uani d 1
H H33 0.3261 0.7515 0.6988 0.020 Uiso calc 1
C C34 0.3063(5) 0.6929(2) 0.63567(17) 0.0157(10) Uani d 1
H H34 0.2980 0.7347 0.6146 0.019 Uiso calc 1
C C35 0.3021(5) 0.6217(2) 0.61428(16) 0.0140(9) Uani d 1
C C36 0.3144(5) 0.5622(2) 0.64719(16) 0.0155(10) Uani d 1
H H36 0.3142 0.5134 0.6346 0.019 Uiso calc 1
C C37 0.3271(5) 0.5742(2) 0.69832(17) 0.0153(10) Uani d 1
C C38 0.2429(6) 0.6721(3) 0.53094(16) 0.0206(11) Uani d 1
H H38A 0.1740 0.7075 0.5495 0.025 Uiso calc 1
H H38B 0.1762 0.6524 0.5032 0.025 Uiso calc 1
C C39 0.3903(7) 0.7128(3) 0.50945(19) 0.0316(13) Uani d 1
H H39A 0.4631 0.6776 0.4928 0.047 Uiso calc 1
H H39B 0.4499 0.7373 0.5364 0.047 Uiso calc 1
H H39C 0.3525 0.7495 0.4853 0.047 Uiso calc 1
C C40 0.3094(5) 0.5399(2) 0.54013(16) 0.0157(10) Uani d 1
H H40A 0.3904 0.5113 0.5596 0.019 Uiso calc 1
H H40B 0.3559 0.5477 0.5065 0.019 Uiso calc 1
C C41 0.1539(6) 0.4950(3) 0.53531(18) 0.0235(11) Uani d 1
H H41A 0.0719 0.5232 0.5167 0.035 Uiso calc 1
H H41B 0.1113 0.4835 0.5685 0.035 Uiso calc 1
H H41C 0.1780 0.4491 0.5176 0.035 Uiso calc 1
C C42 0.4921(5) 0.7074(2) 0.78662(15) 0.0146(9) Uani d 1
C C43 0.6590(5) 0.6963(2) 0.78122(17) 0.0173(10) Uani d 1
H H43 0.7009 0.6508 0.7692 0.021 Uiso calc 1
C C44 0.7637(6) 0.7538(3) 0.79392(16) 0.0202(11) Uani d 1
H H44 0.8789 0.7471 0.7912 0.024 Uiso calc 1
C C45 0.7029(6) 0.8208(3) 0.81042(16) 0.0188(10) Uani d 1
H H45 0.7765 0.8601 0.8171 0.023 Uiso calc 1
C C46 0.5359(6) 0.8311(2) 0.81717(15) 0.0171(10) Uani d 1
H H46 0.4936 0.8761 0.8296 0.021 Uiso calc 1
C C47 0.4327(5) 0.7732(2) 0.80510(15) 0.0140(10) Uani d 1
C C48 0.2526(6) 0.7669(2) 0.80989(15) 0.0143(9) Uani d 1
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'
Br Br -0.2901 2.4595 '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
C1 O1 C13 118.4(3) ?
C24 O2 C7 110.6(3) y
C11 N1 C14 120.6(4) ?
C11 N1 C16 120.7(4) ?
C14 N1 C16 118.1(4) ?
O1 C1 C6 123.5(4) ?
O1 C1 C2 114.9(4) ?
C6 C1 C2 121.6(4) ?
C3 C2 C1 118.7(4) ?
C3 C2 H2 120.7 ?
C1 C2 H2 120.7 ?
C2 C3 C4 121.7(4) ?
C2 C3 Br1 118.9(3) ?
C4 C3 Br1 119.4(3) ?
C5 C4 C3 118.6(4) ?
C5 C4 H4 120.7 ?
C3 C4 H4 120.7 ?
C4 C5 C6 121.1(4) ?
C4 C5 H5 119.4 ?
C6 C5 H5 119.4 ?
C1 C6 C5 118.2(4) ?
C1 C6 C7 121.3(4) ?
C5 C6 C7 120.2(4) ?
C8 C7 C18 113.9(4) y
C8 C7 O2 109.8(3) y
C18 C7 O2 101.8(3) y
C8 C7 C6 110.6(3) y
C18 C7 C6 115.5(3) y
O2 C7 C6 104.3(3) y
C13 C8 C9 115.8(4) ?
C13 C8 C7 122.7(4) ?
C9 C8 C7 121.4(4) ?
C10 C9 C8 122.7(4) ?
C10 C9 H9 118.7 ?
C8 C9 H9 118.7 ?
C9 C10 C11 120.7(4) ?
C9 C10 H10 119.6 ?
C11 C10 H10 119.6 ?
N1 C11 C12 121.1(4) ?
N1 C11 C10 121.7(4) ?
C12 C11 C10 117.1(4) ?
C13 C12 C11 119.8(4) ?
C13 C12 H12 120.1 ?
C11 C12 H12 120.1 ?
C8 C13 O1 122.2(4) ?
C8 C13 C12 123.8(4) ?
O1 C13 C12 114.0(4) ?
N1 C14 C15 112.9(4) ?
N1 C14 H14A 109.0 ?
C15 C14 H14A 109.0 ?
N1 C14 H14B 109.0 ?
C15 C14 H14B 109.0 ?
H14A C14 H14B 107.8 ?
C14 C15 H15A 109.5 ?
C14 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C14 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
N1 C16 C17 114.1(4) ?
N1 C16 H16A 108.7 ?
C17 C16 H16A 108.7 ?
N1 C16 H16B 108.7 ?
C17 C16 H16B 108.7 ?
H16A C16 H16B 107.6 ?
C16 C17 H17A 109.5 ?
C16 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C16 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C23 C18 C19 120.7(4) ?
C23 C18 C7 110.5(4) ?
C19 C18 C7 128.8(4) ?
C20 C19 C18 117.5(4) ?
C20 C19 H19 121.2 ?
C18 C19 H19 121.2 ?
C19 C20 C21 121.7(4) ?
C19 C20 H20 119.2 ?
C21 C20 H20 119.2 ?
C22 C21 C20 121.0(4) ?
C22 C21 H21 119.5 ?
C20 C21 H21 119.5 ?
C21 C22 C23 116.9(4) ?
C21 C22 H22 121.5 ?
C23 C22 H22 121.5 ?
C18 C23 C22 122.1(4) ?
C18 C23 C24 108.9(4) ?
C22 C23 C24 129.0(4) ?
O3 C24 O2 121.1(4) y
O3 C24 C23 131.2(4) ?
O2 C24 C23 107.7(4) y
C25 O4 C37 118.8(3) ?
C48 O5 C31 111.4(3) y
C35 N2 C38 121.5(4) ?
C35 N2 C40 122.7(3) ?
C38 N2 C40 115.8(4) ?
O4 C25 C26 115.6(4) ?
O4 C25 C30 122.9(4) ?
C26 C25 C30 121.5(4) ?
C27 C26 C25 117.8(4) ?
C27 C26 H26 121.1 ?
C25 C26 H26 121.1 ?
C26 C27 C28 122.8(4) ?
C26 C27 Br2 118.3(3) ?
C28 C27 Br2 118.9(3) ?
C27 C28 C29 118.3(4) ?
C27 C28 H28 120.9 ?
C29 C28 H28 120.9 ?
C28 C29 C30 121.2(4) ?
C28 C29 H29 119.4 ?
C30 C29 H29 119.4 ?
C25 C30 C29 118.4(4) ?
C25 C30 C31 121.8(4) ?
C29 C30 C31 119.8(4) ?
O5 C31 C32 108.6(3) y
O5 C31 C30 108.8(3) y
C32 C31 C30 111.1(3) y
O5 C31 C42 102.2(3) y
C32 C31 C42 113.0(3) y
C30 C31 C42 112.6(3) y
C37 C32 C33 116.3(4) ?
C37 C32 C31 122.6(4) ?
C33 C32 C31 121.0(4) ?
C34 C33 C32 122.2(4) ?
C34 C33 H33 118.9 ?
C32 C33 H33 118.9 ?
C33 C34 C35 121.5(4) ?
C33 C34 H34 119.2 ?
C35 C34 H34 119.2 ?
N2 C35 C36 121.7(4) ?
N2 C35 C34 121.6(4) ?
C36 C35 C34 116.6(4) ?
C37 C36 C35 120.4(4) ?
C37 C36 H36 119.8 ?
C35 C36 H36 119.8 ?
O4 C37 C32 122.5(4) ?
O4 C37 C36 114.7(4) ?
C32 C37 C36 122.8(4) ?
N2 C38 C39 113.8(4) ?
N2 C38 H38A 108.8 ?
C39 C38 H38A 108.8 ?
N2 C38 H38B 108.8 ?
C39 C38 H38B 108.8 ?
H38A C38 H38B 107.7 ?
C38 C39 H39A 109.5 ?
C38 C39 H39B 109.5 ?
H39A C39 H39B 109.5 ?
C38 C39 H39C 109.5 ?
H39A C39 H39C 109.5 ?
H39B C39 H39C 109.5 ?
N2 C40 C41 114.3(4) ?
N2 C40 H40A 108.7 ?
C41 C40 H40A 108.7 ?
N2 C40 H40B 108.7 ?
C41 C40 H40B 108.7 ?
H40A C40 H40B 107.6 ?
C40 C41 H41A 109.5 ?
C40 C41 H41B 109.5 ?
H41A C41 H41B 109.5 ?
C40 C41 H41C 109.5 ?
H41A C41 H41C 109.5 ?
H41B C41 H41C 109.5 ?
C47 C42 C43 120.6(4) ?
C47 C42 C31 110.0(4) ?
C43 C42 C31 129.4(4) ?
C42 C43 C44 117.8(4) ?
C42 C43 H43 121.1 ?
C44 C43 H43 121.1 ?
C45 C44 C43 121.3(4) ?
C45 C44 H44 119.4 ?
C43 C44 H44 119.4 ?
C46 C45 C44 120.7(4) ?
C46 C45 H45 119.7 ?
C44 C45 H45 119.7 ?
C47 C46 C45 117.6(4) ?
C47 C46 H46 121.2 ?
C45 C46 H46 121.2 ?
C42 C47 C46 121.9(4) ?
C42 C47 C48 108.2(4) ?
C46 C47 C48 129.9(4) ?
O6 C48 O5 121.3(4) y
O6 C48 C47 130.7(4) ?
O5 C48 C47 108.0(4) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C3 1.893(4) ?
O1 C1 1.373(5) ?
O1 C13 1.389(5) ?
O2 C24 1.379(5) y
O2 C7 1.510(5) y
O3 C24 1.201(5) y
N1 C11 1.379(5) ?
N1 C14 1.455(5) ?
N1 C16 1.466(6) ?
C1 C6 1.376(6) ?
C1 C2 1.394(6) ?
C2 C3 1.374(6) ?
C2 H2 0.9500 ?
C3 C4 1.390(6) ?
C4 C5 1.383(6) ?
C4 H4 0.9500 ?
C5 C6 1.406(6) ?
C5 H5 0.9500 ?
C6 C7 1.516(6) y
C7 C8 1.499(6) y
C7 C18 1.499(6) y
C8 C13 1.376(6) ?
C8 C9 1.403(6) ?
C9 C10 1.371(6) ?
C9 H9 0.9500 ?
C10 C11 1.423(6) ?
C10 H10 0.9500 ?
C11 C12 1.403(6) ?
C12 C13 1.391(6) ?
C12 H12 0.9500 ?
C14 C15 1.522(6) ?
C14 H14A 0.9900 ?
C14 H14B 0.9900 ?
C15 H15A 0.9800 ?
C15 H15B 0.9800 ?
C15 H15C 0.9800 ?
C16 C17 1.524(6) ?
C16 H16A 0.9900 ?
C16 H16B 0.9900 ?
C17 H17A 0.9800 ?
C17 H17B 0.9800 ?
C17 H17C 0.9800 ?
C18 C23 1.377(6) ?
C18 C19 1.398(6) ?
C19 C20 1.376(6) ?
C19 H19 0.9500 ?
C20 C21 1.404(6) ?
C20 H20 0.9500 ?
C21 C22 1.378(6) ?
C21 H21 0.9500 ?
C22 C23 1.402(6) ?
C22 H22 0.9500 ?
C23 C24 1.467(6) y
Br2 C27 1.899(4) ?
O4 C25 1.379(5) ?
O4 C37 1.383(5) ?
O5 C48 1.373(5) y
O5 C31 1.488(5) y
O6 C48 1.200(5) y
N2 C35 1.368(5) ?
N2 C38 1.458(5) ?
N2 C40 1.465(5) ?
C25 C26 1.394(6) ?
C25 C30 1.394(6) ?
C26 C27 1.379(6) ?
C26 H26 0.9500 ?
C27 C28 1.380(6) ?
C28 C29 1.388(6) ?
C28 H28 0.9500 ?
C29 C30 1.396(6) ?
C29 H29 0.9500 ?
C30 C31 1.508(6) y
C31 C32 1.503(6) y
C31 C42 1.513(6) y
C32 C37 1.387(6) ?
C32 C33 1.395(6) ?
C33 C34 1.370(6) ?
C33 H33 0.9500 ?
C34 C35 1.418(6) ?
C34 H34 0.9500 ?
C35 C36 1.401(6) ?
C36 C37 1.394(6) ?
C36 H36 0.9500 ?
C38 C39 1.525(7) ?
C38 H38A 0.9900 ?
C38 H38B 0.9900 ?
C39 H39A 0.9800 ?
C39 H39B 0.9800 ?
C39 H39C 0.9800 ?
C40 C41 1.513(6) ?
C40 H40A 0.9900 ?
C40 H40B 0.9900 ?
C41 H41A 0.9800 ?
C41 H41B 0.9800 ?
C41 H41C 0.9800 ?
C42 C47 1.382(6) ?
C42 C43 1.384(6) ?
C43 C44 1.393(6) ?
C43 H43 0.9500 ?
C44 C45 1.388(6) ?
C44 H44 0.9500 ?
C45 C46 1.386(6) ?
C45 H45 0.9500 ?
C46 C47 1.386(6) ?
C46 H46 0.9500 ?
C47 C48 1.478(6) y
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
C16 H16B Cg 1_655 0.99 2.81 3.583(4) 136
C40 H40A Cg1 . 0.99 2.79 3.534(4) 132
C40 H40B Cg2 . 0.99 2.83 3.580(4) 133
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
C13 O1 C1 C6 3.3(6)
C13 O1 C1 C2 -177.9(4)
O1 C1 C2 C3 -179.0(4)
C6 C1 C2 C3 -0.2(7)
C1 C2 C3 C4 -2.1(7)
C1 C2 C3 Br1 177.4(3)
C2 C3 C4 C5 1.8(7)
Br1 C3 C4 C5 -177.7(3)
C3 C4 C5 C6 0.8(7)
O1 C1 C6 C5 -178.7(4)
C2 C1 C6 C5 2.7(7)
O1 C1 C6 C7 7.1(7)
C2 C1 C6 C7 -171.5(4)
C4 C5 C6 C1 -3.0(7)
C4 C5 C6 C7 171.3(4)
C24 O2 C7 C8 -128.9(4)
C24 O2 C7 C18 -7.9(4)
C24 O2 C7 C6 112.6(3)
C1 C6 C7 C8 -12.5(6)
C5 C6 C7 C8 173.4(4)
C1 C6 C7 C18 -143.7(4)
C5 C6 C7 C18 42.2(5)
C1 C6 C7 O2 105.5(4)
C5 C6 C7 O2 -68.6(5)
C18 C7 C8 C13 141.0(4)
O2 C7 C8 C13 -105.6(4)
C6 C7 C8 C13 9.0(6)
C18 C7 C8 C9 -39.6(5)
O2 C7 C8 C9 73.7(5)
C6 C7 C8 C9 -171.7(4)
C13 C8 C9 C10 -0.3(6)
C7 C8 C9 C10 -179.7(4)
C8 C9 C10 C11 -1.4(7)
C14 N1 C11 C12 174.3(4)
C16 N1 C11 C12 2.9(6)
C14 N1 C11 C10 -9.5(6)
C16 N1 C11 C10 179.0(4)
C9 C10 C11 N1 -173.3(4)
C9 C10 C11 C12 3.0(6)
N1 C11 C12 C13 173.2(4)
C10 C11 C12 C13 -3.1(6)
C9 C8 C13 O1 -179.1(4)
C7 C8 C13 O1 0.3(6)
C9 C8 C13 C12 0.2(6)
C7 C8 C13 C12 179.6(4)
C1 O1 C13 C8 -7.1(6)
C1 O1 C13 C12 173.5(4)
C11 C12 C13 C8 1.6(7)
C11 C12 C13 O1 -179.1(4)
C11 N1 C14 C15 -77.4(5)
C16 N1 C14 C15 94.2(5)
C11 N1 C16 C17 76.2(5)
C14 N1 C16 C17 -95.4(5)
C8 C7 C18 C23 122.5(4)
O2 C7 C18 C23 4.4(4)
C6 C7 C18 C23 -107.9(4)
C8 C7 C18 C19 -54.7(6)
O2 C7 C18 C19 -172.8(4)
C6 C7 C18 C19 74.9(6)
C23 C18 C19 C20 0.8(6)
C7 C18 C19 C20 177.7(4)
C18 C19 C20 C21 -0.7(6)
C19 C20 C21 C22 0.4(7)
C20 C21 C22 C23 -0.2(6)
C19 C18 C23 C22 -0.7(6)
C7 C18 C23 C22 -178.1(4)
C19 C18 C23 C24 177.7(4)
C7 C18 C23 C24 0.3(5)
C21 C22 C23 C18 0.4(6)
C21 C22 C23 C24 -177.7(4)
C7 O2 C24 O3 -171.6(4)
C7 O2 C24 C23 8.4(4)
C18 C23 C24 O3 174.5(4)
C22 C23 C24 O3 -7.2(8)
C18 C23 C24 O2 -5.4(5)
C22 C23 C24 O2 172.8(4)
C37 O4 C25 C26 -177.1(4)
C37 O4 C25 C30 4.2(6)
O4 C25 C26 C27 -177.7(4)
C30 C25 C26 C27 1.1(6)
C25 C26 C27 C28 1.1(7)
C25 C26 C27 Br2 -178.9(3)
C26 C27 C28 C29 -2.1(7)
Br2 C27 C28 C29 177.9(3)
C27 C28 C29 C30 1.0(7)
O4 C25 C30 C29 176.6(4)
C26 C25 C30 C29 -2.1(6)
O4 C25 C30 C31 -4.8(6)
C26 C25 C30 C31 176.5(4)
C28 C29 C30 C25 1.0(7)
C28 C29 C30 C31 -177.6(4)
C48 O5 C31 C32 -116.1(4)
C48 O5 C31 C30 122.8(3)
C48 O5 C31 C42 3.5(4)
C25 C30 C31 O5 122.8(4)
C29 C30 C31 O5 -58.7(5)
C25 C30 C31 C32 3.3(5)
C29 C30 C31 C32 -178.2(4)
C25 C30 C31 C42 -124.7(4)
C29 C30 C31 C42 53.8(5)
O5 C31 C32 C37 -121.2(4)
C30 C31 C32 C37 -1.6(5)
C42 C31 C32 C37 126.2(4)
O5 C31 C32 C33 60.6(5)
C30 C31 C32 C33 -179.8(4)
C42 C31 C32 C33 -52.0(5)
C37 C32 C33 C34 0.9(6)
C31 C32 C33 C34 179.1(4)
C32 C33 C34 C35 -1.1(7)
C38 N2 C35 C36 168.1(4)
C40 N2 C35 C36 -10.5(6)
C38 N2 C35 C34 -11.8(6)
C40 N2 C35 C34 169.5(4)
C33 C34 C35 N2 -179.9(4)
C33 C34 C35 C36 0.1(6)
N2 C35 C36 C37 -178.9(4)
C34 C35 C36 C37 1.1(6)
C25 O4 C37 C32 -2.4(6)
C25 O4 C37 C36 176.8(4)
C33 C32 C37 O4 179.5(4)
C31 C32 C37 O4 1.3(6)
C33 C32 C37 C36 0.4(6)
C31 C32 C37 C36 -177.9(4)
C35 C36 C37 O4 179.4(4)
C35 C36 C37 C32 -1.4(7)
C35 N2 C38 C39 91.9(5)
C40 N2 C38 C39 -89.4(5)
C35 N2 C40 C41 90.8(5)
C38 N2 C40 C41 -87.9(5)
O5 C31 C42 C47 -5.1(4)
C32 C31 C42 C47 111.4(4)
C30 C31 C42 C47 -121.7(4)
O5 C31 C42 C43 175.9(4)
C32 C31 C42 C43 -67.6(6)
C30 C31 C42 C43 59.3(6)
C47 C42 C43 C44 -1.4(7)
C31 C42 C43 C44 177.5(4)
C42 C43 C44 C45 -1.4(7)
C43 C44 C45 C46 3.4(7)
C44 C45 C46 C47 -2.4(6)
C43 C42 C47 C46 2.4(7)
C31 C42 C47 C46 -176.7(4)
C43 C42 C47 C48 -176.1(4)
C31 C42 C47 C48 4.8(5)
C45 C46 C47 C42 -0.4(6)
C45 C46 C47 C48 177.6(4)
C31 O5 C48 O6 179.9(4)
C31 O5 C48 C47 -0.9(4)
C42 C47 C48 O6 176.6(4)
C46 C47 C48 O6 -1.7(8)
C42 C47 C48 O5 -2.5(5)
C46 C47 C48 O5 179.2(4)

_cod_database_fobs_code 2242130
