#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:22:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180335 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/04/7200412.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_7200412
loop_
_publ_author_name
'Zhu, Yuan-Yuan'
'Jiang, Long'
'Li, Zhan-Ting'
_publ_section_title
;
 Intramolecular six-membered N--H⋯Br and N--H⋯I hydrogen
 bonding in aromatic amides in the absence of competing interactions
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              235
_journal_paper_doi               10.1039/b814859g
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C26 H19 I N2 O3'
_chemical_formula_sum            'C26 H19 I N2 O3'
_chemical_formula_weight         534.33
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.2320(10)
_cell_angle_beta                 95.9420(10)
_cell_angle_gamma                111.2940(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4506(9)
_cell_length_b                   9.3577(10)
_cell_length_c                   15.3062(16)
_cell_measurement_reflns_used    3546
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.60
_cell_volume                     1117.9(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5826
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    1.463
_exptl_absorpt_correction_T_max  0.7585
_exptl_absorpt_correction_T_min  0.6680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.009
_refine_diff_density_min         -1.059
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0201P)²+1.3100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0687
_reflns_number_gt                3508
_reflns_number_total             3876
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b814859g.txt
_cod_data_source_block           080701a_0m
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7200412
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.25052(3) 0.53049(3) 0.470878(15) 0.05078(9) Uani 1 1 d . . .
C1 C -0.0384(4) 0.7320(3) 0.4624(2) 0.0339(7) Uani 1 1 d . . .
C2 C 0.0083(4) 0.7683(4) 0.3794(2) 0.0440(8) Uani 1 1 d . . .
H2 H -0.0595 0.7083 0.3297 0.053 Uiso 1 1 calc R . .
C3 C 0.1536(4) 0.8918(4) 0.3700(2) 0.0443(8) Uani 1 1 d . . .
H3 H 0.1853 0.9159 0.3145 0.053 Uiso 1 1 calc R . .
C4 C 0.2511(4) 0.9790(4) 0.4442(2) 0.0382(7) Uani 1 1 d . . .
C5 C 0.2065(4) 0.9483(3) 0.5278(2) 0.0358(7) Uani 1 1 d . . .
H5 H 0.2735 1.0109 0.5769 0.043 Uiso 1 1 calc R . .
C6 C 0.0606(4) 0.8229(3) 0.53733(19) 0.0300(6) Uani 1 1 d . . .
C7 C 0.0081(4) 0.7933(3) 0.62848(18) 0.0294(6) Uani 1 1 d . . .
C8 C 0.1131(3) 0.7681(3) 0.78246(18) 0.0285(6) Uani 1 1 d . . .
C9 C -0.0350(4) 0.6224(3) 0.80206(19) 0.0305(6) Uani 1 1 d . . .
C10 C -0.1315(4) 0.5081(3) 0.7373(2) 0.0401(7) Uani 1 1 d . . .
H10 H -0.1123 0.5209 0.6788 0.048 Uiso 1 1 calc R . .
C11 C -0.2569(4) 0.3743(4) 0.7583(2) 0.0483(8) Uani 1 1 d . . .
H11 H -0.3224 0.2993 0.7138 0.058 Uiso 1 1 calc R . .
C12 C -0.2845(4) 0.3523(4) 0.8446(3) 0.0471(9) Uani 1 1 d . . .
H12 H -0.3673 0.2621 0.8586 0.056 Uiso 1 1 calc R . .
C13 C -0.1890(4) 0.4646(4) 0.9099(2) 0.0447(8) Uani 1 1 d . . .
H13 H -0.2080 0.4505 0.9683 0.054 Uiso 1 1 calc R . .
C14 C -0.0644(4) 0.5988(4) 0.8891(2) 0.0379(7) Uani 1 1 d . . .
H14 H 0.0000 0.6737 0.9338 0.045 Uiso 1 1 calc R . .
C15 C 0.0979(4) 0.9208(3) 0.81362(18) 0.0310(6) Uani 1 1 d . . .
C16 C -0.0443(4) 0.9298(4) 0.8464(2) 0.0430(8) Uani 1 1 d . . .
H16 H -0.1370 0.8401 0.8515 0.052 Uiso 1 1 calc R . .
C17 C -0.0506(5) 1.0717(5) 0.8718(2) 0.0575(10) Uani 1 1 d . . .
H17 H -0.1472 1.0760 0.8942 0.069 Uiso 1 1 calc R . .
C18 C 0.0847(6) 1.2058(4) 0.8643(2) 0.0572(10) Uani 1 1 d . . .
H18 H 0.0804 1.3005 0.8818 0.069 Uiso 1 1 calc R . .
C19 C 0.2254(5) 1.1983(4) 0.8307(3) 0.0534(9) Uani 1 1 d . . .
H19 H 0.3172 1.2884 0.8250 0.064 Uiso 1 1 calc R . .
C20 C 0.2322(4) 1.0576(4) 0.8052(2) 0.0428(8) Uani 1 1 d . . .
H20 H 0.3284 1.0544 0.7819 0.051 Uiso 1 1 calc R . .
C21 C 0.2772(3) 0.7535(3) 0.82867(18) 0.0291(6) Uani 1 1 d . . .
C22 C 0.3459(4) 0.8217(4) 0.9131(2) 0.0360(7) Uani 1 1 d . . .
H22 H 0.2990 0.8852 0.9400 0.043 Uiso 1 1 calc R . .
C23 C 0.4833(4) 0.7966(4) 0.9578(2) 0.0419(8) Uani 1 1 d . . .
H23 H 0.5281 0.8434 1.0143 0.050 Uiso 1 1 calc R . .
C24 C 0.5535(4) 0.7030(4) 0.9192(2) 0.0468(8) Uani 1 1 d . . .
H24 H 0.6448 0.6851 0.9496 0.056 Uiso 1 1 calc R . .
C25 C 0.4885(4) 0.6356(4) 0.8352(2) 0.0471(8) Uani 1 1 d . . .
H25 H 0.5379 0.5743 0.8083 0.057 Uiso 1 1 calc R . .
C26 C 0.3495(4) 0.6587(4) 0.7905(2) 0.0388(7) Uani 1 1 d . . .
H26 H 0.3042 0.6102 0.7344 0.047 Uiso 1 1 calc R . .
N1 N 0.1275(3) 0.7724(3) 0.68692(15) 0.0295(5) Uani 1 1 d . . .
H1 H 0.2150 0.7611 0.6679 0.035 Uiso 1 1 calc R . .
N2 N 0.4107(4) 1.1081(4) 0.4359(2) 0.0520(8) Uani 1 1 d . . .
O1 O -0.1295(3) 0.7911(2) 0.64593(13) 0.0375(5) Uani 1 1 d . . .
O2 O 0.4812(4) 1.1971(3) 0.5002(2) 0.0694(8) Uani 1 1 d . . .
O3 O 0.4671(3) 1.1172(4) 0.3647(2) 0.0745(9) 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'
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'
I I -0.4742 1.8119 '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
C2 C1 C6 120.2(3) . . ?
C2 C1 I1 117.8(2) . . ?
C6 C1 I1 121.9(2) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 122.3(3) . . ?
C3 C4 N2 119.6(3) . . ?
C5 C4 N2 118.1(3) . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 118.9(3) . . ?
C1 C6 C7 121.8(3) . . ?
O1 C7 N1 124.3(3) . . ?
O1 C7 C6 121.5(3) . . ?
N1 C7 C6 114.2(2) . . ?
N1 C8 C15 106.8(2) . . ?
N1 C8 C21 107.6(2) . . ?
C15 C8 C21 111.1(2) . . ?
N1 C8 C9 111.5(2) . . ?
C15 C8 C9 114.4(2) . . ?
C21 C8 C9 105.2(2) . . ?
C10 C9 C14 118.3(3) . . ?
C10 C9 C8 122.5(3) . . ?
C14 C9 C8 119.0(3) . . ?
C9 C10 C11 120.9(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.7(3) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C16 C15 C20 117.9(3) . . ?
C16 C15 C8 123.7(3) . . ?
C20 C15 C8 118.4(3) . . ?
C15 C16 C17 120.7(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 119.2(3) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 121.2(3) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
C22 C21 C26 118.2(3) . . ?
C22 C21 C8 120.9(3) . . ?
C26 C21 C8 120.6(3) . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.7(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.3(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.6(3) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
C7 N1 C8 122.3(2) . . ?
C7 N1 H1 118.9 . . ?
C8 N1 H1 118.9 . . ?
O2 N2 O3 123.9(3) . . ?
O2 N2 C4 118.2(3) . . ?
O3 N2 C4 117.9(3) . . ?
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
I1 C1 2.097(3) . ?
C1 C2 1.388(4) . ?
C1 C6 1.395(4) . ?
C2 C3 1.372(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(4) . ?
C4 N2 1.470(4) . ?
C5 C6 1.385(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.513(4) . ?
C7 O1 1.212(3) . ?
C7 N1 1.352(4) . ?
C8 N1 1.481(3) . ?
C8 C15 1.542(4) . ?
C8 C21 1.544(4) . ?
C8 C9 1.545(4) . ?
C9 C10 1.381(4) . ?
C9 C14 1.392(4) . ?
C10 C11 1.391(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.378(4) . ?
C15 C20 1.390(4) . ?
C16 C17 1.391(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.388(4) . ?
C21 C26 1.389(4) . ?
C22 C23 1.386(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.375(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.387(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N1 H1 0.8600 . ?
N2 O2 1.213(4) . ?
N2 O3 1.228(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.86 2.62 3.388(3) 149.3 2_676
