#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/09/7200933.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_7200933
loop_
_publ_author_name
'Baudron, Stéphane A.'
'Salazar-Mendoza, Domingo'
'Hosseini, Mir Wais'
_publ_section_title
;
 Combination of primary amide and dipyrrin for the elaboration of
 extended architectures built upon both coordination and hydrogen
 bonding
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1245
_journal_paper_doi               10.1039/b901167f
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C16 H15 N3 O'
_chemical_formula_sum            'C16 H15 N3 O'
_chemical_formula_weight         265.31
_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                80.064(2)
_cell_angle_beta                 65.596(2)
_cell_angle_gamma                74.133(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3130(3)
_cell_length_b                   9.5783(3)
_cell_length_c                   9.8020(3)
_cell_measurement_reflns_used    2747
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.29
_cell_volume                     682.08(4)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7482
_diffrn_reflns_theta_full        26.93
_diffrn_reflns_theta_max         26.93
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.9698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       platelet
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0444
_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)+(0.0689P)²+0.2063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1456
_reflns_number_gt                2277
_reflns_number_total             2865
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b901167f.txt
_cod_data_source_block           compound2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_original_sg_symbol_H-M      'P-1 '
_cod_database_code               7200933
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
C1 C -0.0388(3) 0.78913(19) 0.30586(19) 0.0309(4) Uani 1 1 d . . .
H1A H -0.1560 0.8409 0.3193 0.037 Uiso 1 1 calc R . .
C2 C 0.0089(3) 0.64926(19) 0.3590(2) 0.0324(4) Uani 1 1 d . . .
H2A H -0.0693 0.5886 0.4153 0.039 Uiso 1 1 calc R . .
C3 C 0.2001(2) 0.61385(17) 0.31228(18) 0.0269(4) Uani 1 1 d . . .
H3 H 0.2705 0.5252 0.3318 0.032 Uiso 1 1 calc R . .
C4 C 0.2626(2) 0.73396(16) 0.23310(17) 0.0228(4) Uani 1 1 d . . .
C5 C 0.4522(2) 0.75857(16) 0.15494(17) 0.0224(4) Uani 1 1 d . . .
H5 H 0.4752 0.7813 0.0480 0.027 Uiso 1 1 calc R . .
C6 C 0.4725(2) 0.88685(16) 0.21271(17) 0.0234(4) Uani 1 1 d . . .
C7 C 0.3753(2) 0.95596(18) 0.34331(18) 0.0282(4) Uani 1 1 d . . .
H7 H 0.2718 0.9342 0.4208 0.034 Uiso 1 1 calc R . .
C8 C 0.4615(3) 1.06711(19) 0.3389(2) 0.0332(4) Uani 1 1 d . . .
H8 H 0.4242 1.1319 0.4125 0.040 Uiso 1 1 calc R . .
C9 C 0.6092(3) 1.06103(18) 0.2067(2) 0.0334(4) Uani 1 1 d . . .
H9 H 0.6913 1.1208 0.1740 0.040 Uiso 1 1 calc R . .
C10 C 0.5906(2) 0.62043(16) 0.16864(17) 0.0227(4) Uani 1 1 d . . .
C11 C 0.6935(2) 0.53358(17) 0.04876(18) 0.0275(4) Uani 1 1 d . . .
H11 H 0.6782 0.5599 -0.0417 0.033 Uiso 1 1 calc R . .
C12 C 0.8192(3) 0.40768(17) 0.06211(19) 0.0283(4) Uani 1 1 d . . .
H12 H 0.8881 0.3508 -0.0194 0.034 Uiso 1 1 calc R . .
C13 C 0.8420(2) 0.36679(16) 0.19743(18) 0.0253(4) Uani 1 1 d . . .
C14 C 0.7364(3) 0.45186(18) 0.31855(19) 0.0287(4) Uani 1 1 d . . .
H14 H 0.7484 0.4238 0.4102 0.034 Uiso 1 1 calc R . .
C15 C 0.6133(2) 0.57799(18) 0.30408(18) 0.0277(4) Uani 1 1 d . . .
H15 H 0.5451 0.6351 0.3855 0.033 Uiso 1 1 calc R . .
C16 C 0.9847(3) 0.23535(18) 0.2062(2) 0.0307(4) Uani 1 1 d . . .
N1 N 0.1148(2) 0.83967(14) 0.22987(15) 0.0273(3) Uani 1 1 d . . .
H1 H 0.1186 0.9253 0.1862 0.033 Uiso 1 1 calc R . .
N2 N 0.6149(2) 0.95132(15) 0.13087(16) 0.0289(3) Uani 1 1 d . . .
H2 H 0.6961 0.9265 0.0444 0.035 Uiso 1 1 calc R . .
N3 N 1.0396(3) 0.22106(19) 0.3185(2) 0.0564(6) Uani 1 1 d . . .
H3A H 1.1216 0.1466 0.3268 0.068 Uiso 1 1 calc R . .
H3B H 0.9932 0.2863 0.3828 0.068 Uiso 1 1 calc R . .
O1 O 1.04958(18) 0.14298(12) 0.11243(14) 0.0342(3) 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'
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 108.13(16) . . ?
N1 C1 H1A 125.9 . . ?
C2 C1 H1A 125.9 . . ?
C1 C2 C3 107.13(16) . . ?
C1 C2 H2A 126.4 . . ?
C3 C2 H2A 126.4 . . ?
C4 C3 C2 107.65(14) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 H3 126.2 . . ?
N1 C4 C3 107.13(15) . . ?
N1 C4 C5 121.67(13) . . ?
C3 C4 C5 131.17(15) . . ?
C4 C5 C6 111.57(13) . . ?
C4 C5 C10 110.54(12) . . ?
C6 C5 C10 111.67(13) . . ?
C4 C5 H5 107.6 . . ?
C6 C5 H5 107.6 . . ?
C10 C5 H5 107.6 . . ?
N2 C6 C7 107.35(15) . . ?
N2 C6 C5 120.22(14) . . ?
C7 C6 C5 132.38(15) . . ?
C6 C7 C8 107.58(16) . . ?
C6 C7 H7 126.2 . . ?
C8 C7 H7 126.2 . . ?
C9 C8 C7 107.27(16) . . ?
C9 C8 H8 126.4 . . ?
C7 C8 H8 126.4 . . ?
C8 C9 N2 107.74(16) . . ?
C8 C9 H9 126.1 . . ?
N2 C9 H9 126.1 . . ?
C11 C10 C15 118.74(15) . . ?
C11 C10 C5 121.15(13) . . ?
C15 C10 C5 120.11(14) . . ?
C10 C11 C12 120.84(14) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 120.01(15) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.24(15) . . ?
C14 C13 C16 121.87(15) . . ?
C12 C13 C16 118.85(15) . . ?
C15 C14 C13 120.50(15) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 120.65(15) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
O1 C16 N3 121.12(17) . . ?
O1 C16 C13 121.22(16) . . ?
N3 C16 C13 117.66(16) . . ?
C1 N1 C4 109.96(14) . . ?
C1 N1 H1 125.0 . . ?
C4 N1 H1 125.0 . . ?
C6 N2 C9 110.06(15) . . ?
C6 N2 H2 125.0 . . ?
C9 N2 H2 125.0 . . ?
C16 N3 H3A 120.0 . . ?
C16 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
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 1.359(2) . ?
C1 C2 1.365(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.417(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.372(2) . ?
C3 H3 0.9300 . ?
C4 N1 1.370(2) . ?
C4 C5 1.507(2) . ?
C5 C6 1.514(2) . ?
C5 C10 1.525(2) . ?
C5 H5 0.9800 . ?
C6 N2 1.367(2) . ?
C6 C7 1.369(2) . ?
C7 C8 1.423(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.365(3) . ?
C8 H8 0.9300 . ?
C9 N2 1.368(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(2) . ?
C10 C15 1.394(2) . ?
C11 C12 1.390(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(2) . ?
C13 C16 1.493(2) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O1 1.237(2) . ?
C16 N3 1.330(2) . ?
N1 H1 0.8600 . ?
N2 H2 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653583
