#------------------------------------------------------------------------------
#$Date: 2019-08-13 06:13:20 +0300 (Tue, 13 Aug 2019) $
#$Revision: 217508 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/33/7233371.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_7233371
loop_
_publ_author_name
'Cheisson, Thibault'
'Jian, Jiwen'
'Su, Jing'
'Eaton, Teresa M.'
'Gau, Michael'
'Carroll, Patrick'
'Batista, Enrique R.'
'Yang, Ping'
'Gibson, John K.'
'Schelter, Eric J.'
_publ_section_title
;
 Halide Anion Discrimination by a Tripodal Hydroxylamine Ligand in Gas and
 Condensed Phases
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/C9CP03764K
_journal_year                    2019
_chemical_formula_moiety         'C33 H49 N4 O3, 0.5(C6 H6), Br'
_chemical_formula_sum            'C36 H52 Br N4 O3'
_chemical_formula_weight         668.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-06
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2019-03-06 deposited with the CCDC.    2019-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 129.4510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.0180(11)
_cell_length_b                   15.6456(6)
_cell_length_c                   19.7456(7)
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.504
_cell_measurement_theta_min      2.418
_cell_volume                     6922.2(5)
_computing_data_collection
;
Bruker APEX2 v2014.11-0
;
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
;
shelXL v2014/7
;
_computing_structure_solution
;
'shelXS-97'
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30306
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         1.587
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.228
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/4'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             2840
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.571
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         7927
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0418
_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)+(0.0595P)²+12.8587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                6610
_reflns_number_total             7927
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cp03764k3.cif
_cod_data_source_block           40181
_cod_database_code               7233371
_shelx_estimated_absorpt_t_max   0.877
_shelx_estimated_absorpt_t_min   0.653
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
O1 O 0.40576(9) 0.21684(13) 0.45779(13) 0.0397(5) Uani 1 1 d . . .
H1 H 0.3899 0.2567 0.4209 0.060 Uiso 1 1 calc GR . .
O2 O 0.32067(9) 0.24682(11) 0.15653(11) 0.0344(4) Uani 1 1 d . . .
H2 H 0.3226 0.2785 0.1926 0.052 Uiso 1 1 calc GR . .
O3 O 0.08244(7) 0.04041(10) 0.12955(10) 0.0227(3) Uani 1 1 d . . .
H3 H 0.0983 -0.0081 0.1471 0.034 Uiso 1 1 calc GR . .
N1 N 0.35971(10) 0.16879(14) 0.45033(13) 0.0297(5) Uani 1 1 d . . .
N2 N 0.33396(8) 0.15939(12) 0.18823(12) 0.0195(4) Uani 1 1 d . . .
N3 N 0.11691(8) 0.09364(12) 0.11587(11) 0.0183(4) Uani 1 1 d . . .
N4 N 0.24249(9) 0.07183(13) 0.23798(12) 0.0231(4) Uani 1 1 d . . .
H4 H 0.2016 0.0478 0.1929 0.028 Uiso 1 1 calc R . .
C1 C 0.25977(10) 0.05117(17) 0.32718(14) 0.0261(5) Uani 1 1 d . . .
H1a H 0.2525 0.1022 0.3490 0.031 Uiso 1 1 calc R . .
H1b H 0.2338 0.0046 0.3199 0.031 Uiso 1 1 calc R . .
C2 C 0.32446(10) 0.02434(17) 0.39491(14) 0.0258(5) Uani 1 1 d . . .
C3 C 0.33673(12) -0.06324(18) 0.40102(16) 0.0314(6) Uani 1 1 d . . .
H3a H 0.3045 -0.1026 0.3688 0.038 Uiso 1 1 calc R . .
C4 C 0.39440(12) -0.09367(18) 0.45268(18) 0.0352(6) Uani 1 1 d . . .
H4a H 0.4018 -0.1532 0.4549 0.042 Uiso 1 1 calc R . .
C5 C 0.44128(12) -0.03669(19) 0.50113(16) 0.0341(6) Uani 1 1 d . . .
H5 H 0.4811 -0.0571 0.5355 0.041 Uiso 1 1 calc R . .
C6 C 0.43095(11) 0.04890(19) 0.50019(16) 0.0318(6) Uani 1 1 d . . .
H6 H 0.4637 0.0872 0.5346 0.038 Uiso 1 1 calc R . .
C7 C 0.37225(11) 0.08045(16) 0.44863(15) 0.0265(5) Uani 1 1 d . . .
C8 C 0.36472(13) 0.19341(18) 0.52907(16) 0.0350(6) Uani 1 1 d . . .
C9 C 0.34825(16) 0.2864(2) 0.5195(2) 0.0499(8) Uani 1 1 d . . .
H9a H 0.3089 0.2957 0.4624 0.075 Uiso 1 1 calc GR . .
H9b H 0.3780 0.3212 0.5234 0.075 Uiso 1 1 calc GR . .
H9c H 0.3472 0.3029 0.5664 0.075 Uiso 1 1 calc GR . .
C10 C 0.31817(15) 0.1416(2) 0.5253(2) 0.0463(8) Uani 1 1 d . . .
H10a H 0.2784 0.1523 0.4693 0.069 Uiso 1 1 calc GR . .
H10b H 0.3189 0.1589 0.5736 0.069 Uiso 1 1 calc GR . .
H10c H 0.3275 0.0806 0.5304 0.069 Uiso 1 1 calc GR . .
C11 C 0.42676(13) 0.1802(2) 0.61704(17) 0.0457(8) Uani 1 1 d . . .
H11a H 0.4295 0.2103 0.6631 0.069 Uiso 1 1 calc GR . .
H11b H 0.4568 0.2028 0.6139 0.069 Uiso 1 1 calc GR . .
H11c H 0.4337 0.1190 0.6307 0.069 Uiso 1 1 calc GR . .
C12 C 0.28226(10) 0.02883(15) 0.22343(15) 0.0228(5) Uani 1 1 d . . .
H12a H 0.2832 -0.0333 0.2339 0.027 Uiso 1 1 calc R . .
H12b H 0.3234 0.0509 0.2673 0.027 Uiso 1 1 calc R . .
C13 C 0.26306(10) 0.04192(15) 0.13267(15) 0.0211(4) Uani 1 1 d . . .
C14 C 0.22074(10) -0.01347(16) 0.06593(16) 0.0278(5) Uani 1 1 d . . .
H14 H 0.2064 -0.0601 0.0787 0.033 Uiso 1 1 calc R . .
C15 C 0.19949(11) -0.00093(18) -0.01881(17) 0.0326(6) Uani 1 1 d . . .
H15 H 0.1709 -0.0393 -0.0639 0.039 Uiso 1 1 calc R . .
C16 C 0.21952(11) 0.06675(19) -0.03803(15) 0.0339(6) Uani 1 1 d . . .
H16 H 0.2035 0.0763 -0.0969 0.041 Uiso 1 1 calc R . .
C17 C 0.26350(12) 0.12202(16) 0.02852(15) 0.0273(5) Uani 1 1 d . . .
H17 H 0.2772 0.1688 0.0149 0.033 Uiso 1 1 calc R . .
C18 C 0.28683(10) 0.10766(15) 0.11473(14) 0.0204(4) Uani 1 1 d . . .
C19 C 0.39587(11) 0.13858(16) 0.22163(16) 0.0265(5) Uani 1 1 d . . .
C20 C 0.40421(14) 0.1563(2) 0.1536(2) 0.0490(8) Uani 1 1 d . . .
H20a H 0.3925 0.2153 0.1328 0.073 Uiso 1 1 calc GR . .
H20b H 0.3792 0.1169 0.1041 0.073 Uiso 1 1 calc GR . .
H20c H 0.4462 0.1479 0.1806 0.073 Uiso 1 1 calc GR . .
C21 C 0.43789(12) 0.19436(19) 0.30272(17) 0.0339(6) Uani 1 1 d . . .
H21a H 0.4306 0.1845 0.3442 0.051 Uiso 1 1 calc GR . .
H21b H 0.4307 0.2547 0.2854 0.051 Uiso 1 1 calc GR . .
H21c H 0.4793 0.1797 0.3306 0.051 Uiso 1 1 calc GR . .
C22 C 0.40877(11) 0.04483(18) 0.24848(19) 0.0358(6) Uani 1 1 d . . .
H22a H 0.3794 0.0090 0.1977 0.054 Uiso 1 1 calc GR . .
H22b H 0.4062 0.0347 0.2950 0.054 Uiso 1 1 calc GR . .
H22c H 0.4489 0.0305 0.2700 0.054 Uiso 1 1 calc GR . .
C23 C 0.23731(10) 0.16679(15) 0.22185(16) 0.0259(5) Uani 1 1 d . . .
H23a H 0.2303 0.1779 0.1666 0.031 Uiso 1 1 calc R . .
H23b H 0.2754 0.1946 0.2702 0.031 Uiso 1 1 calc R . .
C24 C 0.18705(10) 0.20559(15) 0.21566(15) 0.0214(4) Uani 1 1 d . . .
C25 C 0.19973(10) 0.27929(15) 0.26413(15) 0.0240(5) Uani 1 1 d . . .
H25 H 0.2387 0.3031 0.2985 0.029 Uiso 1 1 calc R . .
C26 C 0.15665(11) 0.31843(16) 0.26319(15) 0.0266(5) Uani 1 1 d . . .
H26 H 0.1657 0.3696 0.2955 0.032 Uiso 1 1 calc R . .
C27 C 0.10039(11) 0.28306(17) 0.21517(16) 0.0284(5) Uani 1 1 d . . .
H27 H 0.0709 0.3096 0.2150 0.034 Uiso 1 1 calc R . .
C28 C 0.08662(10) 0.20886(16) 0.16706(15) 0.0235(5) Uani 1 1 d . . .
H28 H 0.0482 0.1839 0.1355 0.028 Uiso 1 1 calc R . .
C29 C 0.12940(9) 0.17108(14) 0.16521(13) 0.0186(4) Uani 1 1 d . . .
C30 C 0.07923(10) 0.10592(16) 0.01731(14) 0.0230(5) Uani 1 1 d . . .
C31 C 0.11614(12) 0.16002(17) 0.00248(16) 0.0287(5) Uani 1 1 d . . .
H31a H 0.1534 0.1301 0.0265 0.043 Uiso 1 1 calc GR . .
H31b H 0.1253 0.2153 0.0320 0.043 Uiso 1 1 calc GR . .
H31c H 0.0933 0.1693 -0.0605 0.043 Uiso 1 1 calc GR . .
C32 C 0.01926(11) 0.14879(17) -0.02519(16) 0.0302(5) Uani 1 1 d . . .
H32a H 0.0258 0.2087 -0.0066 0.045 Uiso 1 1 calc GR . .
H32b H -0.0011 0.1191 -0.0072 0.045 Uiso 1 1 calc GR . .
H32c H -0.0054 0.1461 -0.0891 0.045 Uiso 1 1 calc GR . .
C33 C 0.06925(11) 0.01673(16) -0.02173(15) 0.0265(5) Uani 1 1 d . . .
H33a H 0.0381 -0.0127 -0.0250 0.040 Uiso 1 1 calc GR . .
H33b H 0.1064 -0.0161 0.0156 0.040 Uiso 1 1 calc GR . .
H33c H 0.0569 0.0219 -0.0807 0.040 Uiso 1 1 calc GR . .
C34 C 0.5000 0.3986(3) 0.2500 0.0301(8) Uani 1 2 d S T P
H34 H 0.5000 0.3378 0.2500 0.036 Uiso 1 2 calc RS T P
C35 C 0.45470(11) 0.44233(19) 0.24025(15) 0.0325(6) Uani 1 1 d . . .
H35 H 0.4236 0.4119 0.2332 0.039 Uiso 1 1 calc R . .
C36 C 0.45502(12) 0.5307(2) 0.24080(16) 0.0375(7) Uani 1 1 d . . .
H36 H 0.4243 0.5611 0.2349 0.045 Uiso 1 1 calc R . .
C37 C 0.5000 0.5747(3) 0.2500 0.0399(10) Uani 1 2 d S T P
H37 H 0.5000 0.6354 0.2500 0.048 Uiso 1 2 calc RS T P
Br1 Br 0.33434(2) 0.36914(2) 0.30424(2) 0.02294(8) Uani 1 1 d . . .
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'
Br Br -0.2901 2.4595 '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
O1 N1 C8 106.32(19) . .
C7 N1 O1 105.63(19) . .
C7 N1 C8 114.1(2) . .
O2 N2 C18 105.72(17) . .
O2 N2 C19 108.01(17) . .
C18 N2 C19 114.93(17) . .
O3 N3 C30 106.86(15) . .
C29 N3 O3 105.18(15) . .
C29 N3 C30 115.07(17) . .
C12 N4 C1 113.18(17) . .
C23 N4 C1 111.57(18) . .
C23 N4 C12 112.58(18) . .
C2 C1 N4 113.01(19) . .
C3 C2 C1 116.8(2) . .
C7 C2 C1 124.8(2) . .
C7 C2 C3 118.3(2) . .
C4 C3 C2 121.6(3) . .
C3 C4 C5 119.2(3) . .
C6 C5 C4 120.7(2) . .
C5 C6 C7 120.5(2) . .
C2 C7 N1 118.6(2) . .
C2 C7 C6 119.4(2) . .
C6 C7 N1 122.0(2) . .
N1 C8 C10 107.9(2) . .
N1 C8 C11 114.1(2) . .
C9 C8 N1 107.5(2) . .
C9 C8 C10 107.8(3) . .
C9 C8 C11 108.9(3) . .
C11 C8 C10 110.4(2) . .
N4 C12 C13 114.39(18) . .
C14 C13 C12 118.4(2) . .
C14 C13 C18 119.8(2) . .
C18 C13 C12 121.8(2) . .
C15 C14 C13 120.3(2) . .
C16 C15 C14 120.2(2) . .
C15 C16 C17 120.6(2) . .
C18 C17 C16 119.4(2) . .
C13 C18 N2 117.25(19) . .
C17 C18 N2 123.3(2) . .
C17 C18 C13 119.4(2) . .
N2 C19 C20 112.7(2) . .
N2 C19 C21 105.75(19) . .
N2 C19 C22 108.78(19) . .
C21 C19 C20 110.5(2) . .
C22 C19 C20 109.8(2) . .
C22 C19 C21 109.2(2) . .
N4 C23 C24 112.00(19) . .
C25 C24 C23 117.2(2) . .
C25 C24 C29 118.9(2) . .
C29 C24 C23 123.9(2) . .
C26 C25 C24 121.1(2) . .
C27 C26 C25 119.8(2) . .
C26 C27 C28 120.4(2) . .
C27 C28 C29 119.9(2) . .
C24 C29 N3 118.41(19) . .
C28 C29 N3 121.66(19) . .
C28 C29 C24 119.8(2) . .
N3 C30 C31 107.02(18) . .
N3 C30 C32 113.61(19) . .
N3 C30 C33 106.34(18) . .
C32 C30 C31 110.1(2) . .
C32 C30 C33 109.8(2) . .
C33 C30 C31 109.8(2) . .
C35 C34 C35 120.6(4) . 2_655
C36 C35 C34 119.5(3) . .
C37 C36 C35 120.0(3) . .
C36 C37 C36 120.2(4) 2_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.457(3) .
O2 N2 1.451(2) .
O3 N3 1.453(2) .
N1 C7 1.435(3) .
N1 C8 1.516(3) .
N2 C18 1.452(3) .
N2 C19 1.504(3) .
N3 C29 1.449(3) .
N3 C30 1.522(3) .
N4 C1 1.528(3) .
N4 C12 1.513(3) .
N4 C23 1.507(3) .
C1 C2 1.516(3) .
C2 C3 1.402(4) .
C2 C7 1.396(3) .
C3 C4 1.378(4) .
C4 C5 1.381(4) .
C5 C6 1.370(4) .
C6 C7 1.406(3) .
C8 C9 1.506(4) .
C8 C10 1.536(4) .
C8 C11 1.525(4) .
C12 C13 1.515(3) .
C13 C14 1.392(3) .
C13 C18 1.404(3) .
C14 C15 1.381(4) .
C15 C16 1.372(4) .
C16 C17 1.404(4) .
C17 C18 1.394(3) .
C19 C20 1.533(3) .
C19 C21 1.527(3) .
C19 C22 1.523(4) .
C23 C24 1.511(3) .
C24 C25 1.390(3) .
C24 C29 1.401(3) .
C25 C26 1.382(3) .
C26 C27 1.380(4) .
C27 C28 1.388(3) .
C28 C29 1.396(3) .
C30 C31 1.532(3) .
C30 C32 1.525(3) .
C30 C33 1.530(3) .
C34 C35 1.383(3) .
C34 C35 1.383(3) 2_655
C35 C36 1.382(4) .
C36 C37 1.382(4) .
C37 C36 1.382(4) 2_655
