#------------------------------------------------------------------------------
#$Date: 2016-03-26 01:38:45 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180149 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/46/7104602.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_7104602
loop_
_publ_author_name
'Kitson, Philip J'
'Parenty, Alexis D C'
'Richmond, Craig J'
'Long, De-Liang'
'Cronin, Leroy'
_publ_section_title
;
 A new C-C bond forming annulation reaction leading to pH switchable
 heterocycles.
;
_journal_issue                   27
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4067
_journal_page_last               4069
_journal_paper_doi               10.1039/b905383b
_journal_volume                  34
_journal_year                    2009
_chemical_formula_sum            'C24 H17 N O2'
_chemical_formula_weight         351.39
_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                98.758(4)
_cell_angle_beta                 97.634(4)
_cell_angle_gamma                97.453(3)
_cell_formula_units_Z            2
_cell_length_a                   6.2544(4)
_cell_length_b                   11.5568(8)
_cell_length_c                   11.9526(6)
_cell_measurement_reflns_used    7219
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.41
_cell_volume                     836.33(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'ω 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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10103
_diffrn_reflns_theta_full        25.48
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9756
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.23
_refine_diff_density_rms         0.05
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0481
_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)+(0.0390P)²+0.2417P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                1965
_reflns_number_total             3106
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905383b.txt
_cod_data_source_block           pk514
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7104602
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
O1 O -0.3168(2) 0.51765(14) 0.38868(12) 0.0271(4) Uani 1 1 d . . .
O2 O 0.2873(2) 0.81286(14) 0.40034(13) 0.0327(4) Uani 1 1 d . . .
N1 N 0.1179(3) 0.63656(16) 0.16931(14) 0.0234(5) Uani 1 1 d . . .
C1 C 0.1488(3) 0.66735(19) 0.06538(17) 0.0195(5) Uani 1 1 d . . .
C2 C 0.3070(3) 0.62385(19) 0.00511(18) 0.0247(6) Uani 1 1 d . . .
H2 H 0.3935 0.5709 0.0357 0.030 Uiso 1 1 calc R . .
C3 C 0.3387(4) 0.6572(2) -0.09845(19) 0.0289(6) Uani 1 1 d . . .
H3 H 0.4478 0.6276 -0.1380 0.035 Uiso 1 1 calc R . .
C4 C 0.2123(4) 0.7334(2) -0.14494(19) 0.0293(6) Uani 1 1 d . . .
H4 H 0.2310 0.7543 -0.2173 0.035 Uiso 1 1 calc R . .
C5 C 0.0589(4) 0.7787(2) -0.08477(18) 0.0269(6) Uani 1 1 d . . .
H5 H -0.0265 0.8315 -0.1164 0.032 Uiso 1 1 calc R . .
C6 C 0.0262(3) 0.74901(19) 0.02133(17) 0.0201(5) Uani 1 1 d . . .
C7 C -0.1262(3) 0.80227(19) 0.09079(17) 0.0194(5) Uani 1 1 d . . .
C8 C -0.2262(3) 0.8976(2) 0.06264(18) 0.0246(5) Uani 1 1 d . . .
H8 H -0.1904 0.9315 -0.0013 0.030 Uiso 1 1 calc R . .
C9 C -0.3753(3) 0.9439(2) 0.12492(18) 0.0249(6) Uani 1 1 d . . .
H9 H -0.4402 1.0090 0.1041 0.030 Uiso 1 1 calc R . .
C10 C -0.4299(3) 0.89486(19) 0.21802(18) 0.0226(5) Uani 1 1 d . . .
H10 H -0.5357 0.9245 0.2600 0.027 Uiso 1 1 calc R . .
C11 C -0.3292(3) 0.80256(19) 0.24937(17) 0.0211(5) Uani 1 1 d . . .
H11 H -0.3651 0.7700 0.3141 0.025 Uiso 1 1 calc R . .
C12 C -0.1765(3) 0.75631(18) 0.18817(17) 0.0177(5) Uani 1 1 d . . .
C13 C -0.0805(3) 0.64924(19) 0.21739(16) 0.0198(5) Uani 1 1 d . . .
H13 H -0.1901 0.5773 0.1836 0.024 Uiso 1 1 calc R . .
C14 C 0.2305(4) 0.5496(2) 0.21919(18) 0.0246(5) Uani 1 1 d . . .
H14A H 0.3905 0.5749 0.2327 0.029 Uiso 1 1 calc R . .
H14B H 0.1961 0.4713 0.1684 0.029 Uiso 1 1 calc R . .
C15 C 0.1434(3) 0.5444(2) 0.33275(18) 0.0246(5) Uani 1 1 d . . .
H15A H 0.2655 0.5594 0.3975 0.030 Uiso 1 1 calc R . .
H15B H 0.0581 0.4656 0.3311 0.030 Uiso 1 1 calc R . .
C16 C -0.0036(3) 0.64185(19) 0.34578(17) 0.0189(5) Uani 1 1 d . . .
C17 C -0.1892(3) 0.6096(2) 0.41175(17) 0.0202(5) Uani 1 1 d . . .
C18 C -0.1849(3) 0.70876(19) 0.50743(17) 0.0199(5) Uani 1 1 d . . .
C19 C -0.3279(3) 0.7226(2) 0.58583(18) 0.0251(6) Uani 1 1 d . . .
H19 H -0.4467 0.6625 0.5860 0.030 Uiso 1 1 calc R . .
C20 C -0.2913(4) 0.8274(2) 0.66394(18) 0.0300(6) Uani 1 1 d . . .
H20 H -0.3888 0.8400 0.7176 0.036 Uiso 1 1 calc R . .
C21 C -0.1149(4) 0.9148(2) 0.66557(18) 0.0293(6) Uani 1 1 d . . .
H21 H -0.0941 0.9858 0.7201 0.035 Uiso 1 1 calc R . .
C22 C 0.0305(4) 0.8995(2) 0.58898(17) 0.0253(6) Uani 1 1 d . . .
H22 H 0.1534 0.9580 0.5912 0.030 Uiso 1 1 calc R . .
C23 C -0.0089(3) 0.79603(19) 0.50868(16) 0.0193(5) Uani 1 1 d . . .
C24 C 0.1158(3) 0.7595(2) 0.41567(17) 0.0214(5) 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
O O 0.0106 0.0060 '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'
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'
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
C1 N1 C13 122.52(17) . . ?
C1 N1 C14 123.08(17) . . ?
C13 N1 C14 110.37(17) . . ?
N1 C1 C2 121.3(2) . . ?
N1 C1 C6 119.29(18) . . ?
C2 C1 C6 119.3(2) . . ?
C3 C2 C1 120.7(2) . . ?
C2 C3 C4 120.4(2) . . ?
C5 C4 C3 119.2(2) . . ?
C4 C5 C6 121.8(2) . . ?
C5 C6 C1 118.48(19) . . ?
C5 C6 C7 122.8(2) . . ?
C1 C6 C7 118.69(19) . . ?
C8 C7 C12 117.82(19) . . ?
C8 C7 C6 122.2(2) . . ?
C12 C7 C6 120.00(19) . . ?
C9 C8 C7 122.0(2) . . ?
C8 C9 C10 119.6(2) . . ?
C11 C10 C9 119.5(2) . . ?
C10 C11 C12 121.3(2) . . ?
C11 C12 C7 119.6(2) . . ?
C11 C12 C13 120.92(19) . . ?
C7 C12 C13 119.14(17) . . ?
N1 C13 C12 112.09(17) . . ?
N1 C13 C16 101.16(15) . . ?
C12 C13 C16 119.48(17) . . ?
N1 C14 C15 104.23(16) . . ?
C14 C15 C16 106.25(17) . . ?
C24 C16 C17 103.40(16) . . ?
C24 C16 C15 113.44(17) . . ?
C17 C16 C15 112.14(18) . . ?
C24 C16 C13 113.08(18) . . ?
C17 C16 C13 114.16(16) . . ?
C15 C16 C13 101.04(15) . . ?
O1 C17 C18 126.7(2) . . ?
O1 C17 C16 124.89(19) . . ?
C18 C17 C16 108.44(18) . . ?
C19 C18 C23 121.10(19) . . ?
C19 C18 C17 129.4(2) . . ?
C23 C18 C17 109.53(18) . . ?
C20 C19 C18 117.5(2) . . ?
C19 C20 C21 121.5(2) . . ?
C22 C21 C20 120.9(2) . . ?
C21 C22 C23 117.8(2) . . ?
C22 C23 C18 121.16(19) . . ?
C22 C23 C24 128.8(2) . . ?
C18 C23 C24 110.07(18) . . ?
O2 C24 C23 125.5(2) . . ?
O2 C24 C16 126.19(19) . . ?
C23 C24 C16 108.30(17) . . ?
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
O1 C17 1.214(2) . ?
O2 C24 1.216(2) . ?
N1 C1 1.374(3) . ?
N1 C13 1.450(2) . ?
N1 C14 1.455(3) . ?
C1 C2 1.400(3) . ?
C1 C6 1.410(3) . ?
C2 C3 1.382(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.382(3) . ?
C5 C6 1.397(3) . ?
C6 C7 1.478(3) . ?
C7 C8 1.397(3) . ?
C7 C12 1.407(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.385(3) . ?
C10 C11 1.381(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.511(3) . ?
C13 C16 1.565(3) . ?
C14 C15 1.535(3) . ?
C15 C16 1.546(3) . ?
C16 C24 1.526(3) . ?
C16 C17 1.526(3) . ?
C17 C18 1.486(3) . ?
C18 C19 1.385(3) . ?
C18 C23 1.390(3) . ?
C19 C20 1.385(3) . ?
C20 C21 1.391(3) . ?
C21 C22 1.382(3) . ?
C22 C23 1.387(3) . ?
C23 C24 1.481(3) . ?
