#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:59:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178454 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/75/4027522.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_4027522
loop_
_publ_author_name
'Bowen Fang'
'Huaiji Zheng'
'Changgui Zhao'
'Peng Jing'
'Huilin Li'
'Xingang Xie'
'Xuegong She'
_publ_section_title
;
 Synthesis of the Tetracyclic Core (ABCE Rings) of Daphenylline
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8367
_journal_page_last               8373
_journal_paper_doi               10.1021/jo301533f
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_sum            'C15 H17 N O2'
_chemical_formula_weight         243.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.360(2)
_cell_length_b                   8.125(3)
_cell_length_c                   20.588(7)
_cell_measurement_reflns_used    2222
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.89
_cell_measurement_theta_min      2.69
_cell_volume                     1231.2(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8831
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_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)+(0.0454P)²+0.0049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0944
_reflns_number_gt                1815
_reflns_number_total             2286
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301533f_si_002.cif
_cod_data_source_block           p212121
_cod_original_cell_volume        1231.1(7)
_cod_database_code               4027522
loop_
_symmetry_equiv_pos_as_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_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
C1 C 0.3355(3) 0.8439(2) 0.11210(9) 0.0339(5) Uani 1 1 d .
C2 C 0.2176(3) 0.9740(2) 0.12208(9) 0.0368(5) Uani 1 1 d .
H2 H 0.1233 0.9630 0.1518 0.044 Uiso 1 1 calc R
C3 C 0.2376(3) 1.1199(2) 0.08855(9) 0.0408(5) Uani 1 1 d .
C4 C 0.3774(3) 1.1363(3) 0.04428(10) 0.0479(6) Uani 1 1 d .
H4 H 0.3913 1.2338 0.0211 0.057 Uiso 1 1 calc R
C5 C 0.4951(3) 1.0088(3) 0.03470(10) 0.0455(6) Uani 1 1 d .
H5 H 0.5897 1.0217 0.0052 0.055 Uiso 1 1 calc R
C6 C 0.4782(3) 0.8601(3) 0.06764(9) 0.0365(5) Uani 1 1 d .
C7 C 0.6118(3) 0.7229(3) 0.05333(10) 0.0442(6) Uani 1 1 d .
H7 H 0.6473 0.7269 0.0075 0.053 Uiso 1 1 calc R
C8 C 0.5268(3) 0.5582(3) 0.06818(10) 0.0498(6) Uani 1 1 d .
H8A H 0.4271 0.5369 0.0385 0.060 Uiso 1 1 calc R
H8B H 0.6160 0.4712 0.0633 0.060 Uiso 1 1 calc R
C9 C 0.4584(3) 0.5636(3) 0.13700(10) 0.0453(6) Uani 1 1 d .
H9 H 0.4199 0.4529 0.1500 0.054 Uiso 1 1 calc R
C10 C 0.3034(3) 0.6829(2) 0.14817(9) 0.0408(5) Uani 1 1 d .
H10 H 0.1892 0.6333 0.1334 0.049 Uiso 1 1 calc R
C11 C 0.7803(3) 0.7364(3) 0.09593(11) 0.0533(6) Uani 1 1 d .
H11A H 0.8651 0.6500 0.0842 0.064 Uiso 1 1 calc R
H11B H 0.8390 0.8413 0.0878 0.064 Uiso 1 1 calc R
C12 C 0.7364(3) 0.7228(3) 0.16685(11) 0.0499(6) Uani 1 1 d .
C13 C 0.4959(4) 0.6590(3) 0.24371(11) 0.0597(7) Uani 1 1 d .
H13A H 0.5490 0.7520 0.2663 0.072 Uiso 1 1 calc R
H13B H 0.4983 0.5640 0.2723 0.072 Uiso 1 1 calc R
C14 C 0.3020(3) 0.6976(3) 0.22264(11) 0.0585(7) Uani 1 1 d .
H14A H 0.2677 0.8079 0.2359 0.070 Uiso 1 1 calc R
H14B H 0.2172 0.6198 0.2416 0.070 Uiso 1 1 calc R
C15 C -0.0139(3) 1.2466(3) 0.14175(12) 0.0682(7) Uani 1 1 d .
H15A H -0.1001 1.1635 0.1295 0.102 Uiso 1 1 calc R
H15B H -0.0739 1.3513 0.1443 0.102 Uiso 1 1 calc R
H15C H 0.0372 1.2198 0.1833 0.102 Uiso 1 1 calc R
N1 N 0.5950(2) 0.6249(2) 0.18380(8) 0.0469(5) Uani 1 1 d .
O1 O 0.1269(2) 1.25432(19) 0.09457(7) 0.0607(5) Uani 1 1 d .
O2 O 0.8244(2) 0.8001(2) 0.20726(8) 0.0774(6) 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
C2 C1 C6 119.78(18)
C2 C1 C10 119.11(16)
C6 C1 C10 121.08(18)
C3 C2 C1 121.01(18)
C3 C2 H2 119.5
C1 C2 H2 119.5
O1 C3 C2 125.21(19)
O1 C3 C4 115.26(18)
C2 C3 C4 119.5(2)
C5 C4 C3 119.66(19)
C5 C4 H4 120.2
C3 C4 H4 120.2
C4 C5 C6 122.2(2)
C4 C5 H5 118.9
C6 C5 H5 118.9
C5 C6 C1 117.86(19)
C5 C6 C7 119.09(18)
C1 C6 C7 123.04(18)
C8 C7 C6 110.12(17)
C8 C7 C11 106.58(18)
C6 C7 C11 111.29(16)
C8 C7 H7 109.6
C6 C7 H7 109.6
C11 C7 H7 109.6
C9 C8 C7 107.70(17)
C9 C8 H8A 110.2
C7 C8 H8A 110.2
C9 C8 H8B 110.2
C7 C8 H8B 110.2
H8A C8 H8B 108.5
N1 C9 C8 113.33(18)
N1 C9 C10 101.38(16)
C8 C9 C10 114.42(19)
N1 C9 H9 109.1
C8 C9 H9 109.1
C10 C9 H9 109.1
C9 C10 C1 111.02(17)
C9 C10 C14 101.89(17)
C1 C10 C14 114.86(17)
C9 C10 H10 109.6
C1 C10 H10 109.6
C14 C10 H10 109.6
C12 C11 C7 112.33(18)
C12 C11 H11A 109.1
C7 C11 H11A 109.1
C12 C11 H11B 109.1
C7 C11 H11B 109.1
H11A C11 H11B 107.9
O2 C12 N1 122.1(2)
O2 C12 C11 120.6(2)
N1 C12 C11 117.34(19)
N1 C13 C14 105.46(19)
N1 C13 H13A 110.7
C14 C13 H13A 110.7
N1 C13 H13B 110.7
C14 C13 H13B 110.7
H13A C13 H13B 108.8
C13 C14 C10 105.16(19)
C13 C14 H14A 110.7
C10 C14 H14A 110.7
C13 C14 H14B 110.7
C10 C14 H14B 110.7
H14A C14 H14B 108.8
O1 C15 H15A 109.5
O1 C15 H15B 109.5
H15A C15 H15B 109.5
O1 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C12 N1 C13 119.34(19)
C12 N1 C9 123.50(18)
C13 N1 C9 105.95(18)
C3 O1 C15 117.46(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.383(3)
C1 C6 1.399(3)
C1 C10 1.523(3)
C2 C3 1.380(3)
C2 H2 0.9300
C3 O1 1.368(2)
C3 C4 1.381(3)
C4 C5 1.365(3)
C4 H4 0.9300
C5 C6 1.391(3)
C5 H5 0.9300
C6 C7 1.515(3)
C7 C8 1.508(3)
C7 C11 1.523(3)
C7 H7 0.9800
C8 C9 1.504(3)
C8 H8A 0.9700
C8 H8B 0.9700
C9 N1 1.479(3)
C9 C10 1.515(3)
C9 H9 0.9800
C10 C14 1.538(3)
C10 H10 0.9800
C11 C12 1.500(3)
C11 H11A 0.9700
C11 H11B 0.9700
C12 O2 1.227(3)
C12 N1 1.355(3)
C13 N1 1.459(3)
C13 C14 1.525(3)
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9700
C14 H14B 0.9700
C15 O1 1.421(3)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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
C6 C1 C2 C3 0.4(3)
C10 C1 C2 C3 -177.50(18)
C1 C2 C3 O1 179.22(17)
C1 C2 C3 C4 0.1(3)
O1 C3 C4 C5 -179.87(18)
C2 C3 C4 C5 -0.6(3)
C3 C4 C5 C6 0.8(3)
C4 C5 C6 C1 -0.4(3)
C4 C5 C6 C7 178.69(18)
C2 C1 C6 C5 -0.2(3)
C10 C1 C6 C5 177.61(18)
C2 C1 C6 C7 -179.24(17)
C10 C1 C6 C7 -1.4(3)
C5 C6 C7 C8 -154.26(18)
C1 C6 C7 C8 24.8(2)
C5 C6 C7 C11 87.8(2)
C1 C6 C7 C11 -93.2(2)
C6 C7 C8 C9 -54.0(2)
C11 C7 C8 C9 66.8(2)
C7 C8 C9 N1 -49.4(2)
C7 C8 C9 C10 66.2(2)
N1 C9 C10 C1 80.7(2)
C8 C9 C10 C1 -41.7(2)
N1 C9 C10 C14 -42.1(2)
C8 C9 C10 C14 -164.44(18)
C2 C1 C10 C9 -173.25(17)
C6 C1 C10 C9 8.9(3)
C2 C1 C10 C14 -58.3(3)
C6 C1 C10 C14 123.84(19)
C8 C7 C11 C12 -58.7(2)
C6 C7 C11 C12 61.4(2)
C7 C11 C12 O2 -146.5(2)
C7 C11 C12 N1 32.4(3)
N1 C13 C14 C10 -0.2(2)
C9 C10 C14 C13 26.2(2)
C1 C10 C14 C13 -93.9(2)
O2 C12 N1 C13 25.6(3)
C11 C12 N1 C13 -153.3(2)
O2 C12 N1 C9 164.2(2)
C11 C12 N1 C9 -14.7(3)
C14 C13 N1 C12 118.0(2)
C14 C13 N1 C9 -27.0(2)
C8 C9 N1 C12 23.8(3)
C10 C9 N1 C12 -99.3(2)
C8 C9 N1 C13 166.91(19)
C10 C9 N1 C13 43.8(2)
C2 C3 O1 C15 3.8(3)
C4 C3 O1 C15 -177.06(17)
