#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/76/2017675.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2017675
loop_
_publ_author_name
'Yepes, Andrés F.'
'Jaimes, Ederson'
'Bahsas, Ali'
'Palma, Alirio'
'Hursthouse, Michael B.'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 Ring conformations and intermolecular interactions in two fused
 dibenzoazocines
;
_journal_coeditor_code           GG3233
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o284
_journal_page_last               o288
_journal_paper_doi               10.1107/S0108270110014708
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H20 Cl N O'
_chemical_formula_moiety         'C19 H20 Cl N O'
_chemical_formula_sum            'C19 H20 Cl N O'
_chemical_formula_weight         313.81
_chemical_name_systematic
;
5-Acetyl-2-chloro-8,11-dimethyl-5,6,11,12-
tetrahydrodibenzo[b,f]azocine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 106.683(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3396(3)
_cell_length_b                   21.7131(7)
_cell_length_c                   9.2010(3)
_cell_measurement_reflns_used    3134
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.06
_cell_volume                     1595.97(9)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker Nonius APEXII CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20184
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.376
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0552
_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)+(0.0602P)²+1.5414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1428
_reflns_number_gt                2342
_reflns_number_total             3134
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3233.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017675
_cod_database_fobs_code          2017675
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2017(3) 0.28868(11) 0.2854(3) 0.0249(5) Uani d . 1 . .
H H1 0.1770 0.2532 0.2225 0.030 Uiso calc R 1 . .
C C2 0.1000(3) 0.30406(12) 0.3754(3) 0.0268(6) Uani d . 1 . .
C C3 0.1288(3) 0.35604(12) 0.4659(3) 0.0280(6) Uani d . 1 . .
H H3 0.0575 0.3664 0.5262 0.034 Uiso calc R 1 . .
C C4 0.2649(3) 0.39264(11) 0.4658(3) 0.0253(5) Uani d . 1 . .
H H4 0.2857 0.4291 0.5255 0.030 Uiso calc R 1 . .
C C4a 0.3715(3) 0.37705(11) 0.3800(3) 0.0209(5) Uani d . 1 . .
N N5 0.5143(2) 0.41542(9) 0.3883(2) 0.0213(4) Uani d . 1 . .
C C6 0.4946(3) 0.46898(11) 0.2845(3) 0.0286(6) Uani d . 1 . .
H H6A 0.6067 0.4814 0.2784 0.034 Uiso calc R 1 . .
H H6B 0.4481 0.5039 0.3287 0.034 Uiso calc R 1 . .
C C6a 0.3829(3) 0.45748(11) 0.1253(3) 0.0223(5) Uani d . 1 . .
C C7 0.2713(3) 0.50441(12) 0.0594(3) 0.0283(6) Uani d . 1 . .
H H7 0.2652 0.5401 0.1172 0.034 Uiso calc R 1 . .
C C8 0.1681(3) 0.49997(14) -0.0903(3) 0.0360(7) Uani d . 1 . .
C C9 0.1777(4) 0.44593(14) -0.1695(3) 0.0403(7) Uani d . 1 . .
H H9 0.1061 0.4408 -0.2697 0.048 Uiso calc R 1 . .
C C10 0.2898(4) 0.39975(13) -0.1048(3) 0.0373(7) Uani d . 1 . .
H H10 0.2941 0.3636 -0.1616 0.045 Uiso calc R 1 . .
C C10a 0.3963(3) 0.40527(11) 0.0419(3) 0.0283(6) Uani d . 1 . .
C C11 0.5255(3) 0.35585(12) 0.1110(3) 0.0290(6) Uani d . 1 . .
H H11 0.6187 0.3761 0.1899 0.035 Uiso calc R 1 . .
C C12 0.4512(3) 0.30549(11) 0.1901(3) 0.0270(6) Uani d . 1 . .
H H12A 0.3857 0.2772 0.1108 0.032 Uiso calc R 1 . .
H H12B 0.5454 0.2814 0.2555 0.032 Uiso calc R 1 . .
C C12a 0.3401(3) 0.32503(11) 0.2865(3) 0.0217(5) Uani d . 1 . .
C C13 0.6012(4) 0.32533(13) -0.0038(4) 0.0420(7) Uani d . 1 . .
H H13A 0.5139 0.3026 -0.0787 0.063 Uiso calc R 1 . .
H H13B 0.6898 0.2968 0.0491 0.063 Uiso calc R 1 . .
H H13C 0.6485 0.3570 -0.0553 0.063 Uiso calc R 1 . .
Cl Cl1 -0.06912(9) 0.25649(3) 0.37367(8) 0.0407(2) Uani d . 1 . .
O O51 0.7817(2) 0.44253(9) 0.5061(2) 0.0335(5) Uani d . 1 . .
C C51 0.6633(3) 0.40767(11) 0.4966(3) 0.0245(5) Uani d . 1 . .
C C52 0.6774(3) 0.35412(13) 0.6025(3) 0.0343(6) Uani d . 1 . .
H H52A 0.7888 0.3539 0.6760 0.051 Uiso calc R 1 . .
H H52B 0.6604 0.3157 0.5442 0.051 Uiso calc R 1 . .
H H52C 0.5921 0.3578 0.6564 0.051 Uiso calc R 1 . .
C C81 0.0565(4) 0.55202(16) -0.1646(4) 0.0507(9) Uani d . 1 . .
H H81A 0.1112 0.5758 -0.2273 0.076 Uiso calc R 1 . .
H H81B 0.0349 0.5788 -0.0865 0.076 Uiso calc R 1 . .
H H81C -0.0497 0.5355 -0.2285 0.076 Uiso calc R 1 . .
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C12a . . 120.4(2) ?
C2 C1 H1 . . 119.8 ?
C12a C1 H1 . . 119.8 ?
C3 C2 C1 . . 121.8(2) ?
C3 C2 Cl1 . . 119.28(19) ?
C1 C2 Cl1 . . 118.9(2) ?
C2 C3 C4 . . 118.0(2) ?
C2 C3 H3 . . 121.0 ?
C4 C3 H3 . . 121.0 ?
C3 C4 C4a . . 121.2(2) ?
C3 C4 H4 . . 119.4 ?
C4a C4 H4 . . 119.4 ?
C4 C4a C12a . . 120.6(2) ?
C4 C4a N5 . . 119.0(2) ?
C12a C4a N5 . . 120.4(2) ?
C51 N5 C4a . . 122.4(2) ?
C51 N5 C6 . . 118.5(2) ?
C4a N5 C6 . . 118.92(19) ?
N5 C6 C6a . . 114.6(2) ?
N5 C6 H6A . . 108.6 ?
C6a C6 H6A . . 108.6 ?
N5 C6 H6B . . 108.6 ?
C6a C6 H6B . . 108.6 ?
H6A C6 H6B . . 107.6 ?
C10a C6a C7 . . 120.3(2) ?
C10a C6a C6 . . 122.9(2) ?
C7 C6a C6 . . 116.6(2) ?
C6a C7 C8 . . 121.4(3) ?
C6a C7 H7 . . 119.3 ?
C8 C7 H7 . . 119.3 ?
C9 C8 C7 . . 117.4(3) ?
C9 C8 C81 . . 121.1(3) ?
C7 C8 C81 . . 121.5(3) ?
C10 C9 C8 . . 121.2(3) ?
C10 C9 H9 . . 119.4 ?
C8 C9 H9 . . 119.4 ?
C9 C10 C10a . . 121.3(3) ?
C9 C10 H10 . . 119.4 ?
C10a C10 H10 . . 119.4 ?
C6a C10a C10 . . 118.4(2) ?
C6a C10a C11 . . 120.2(2) ?
C10 C10a C11 . . 121.5(2) ?
C10a C11 C13 . . 113.6(2) ?
C10a C11 C12 . . 111.4(2) ?
C13 C11 C12 . . 108.7(2) ?
C10a C11 H11 . . 107.6 ?
C13 C11 H11 . . 107.6 ?
C12 C11 H11 . . 107.6 ?
C12a C12 C11 . . 118.3(2) ?
C12a C12 H12A . . 107.7 ?
C11 C12 H12A . . 107.7 ?
C12a C12 H12B . . 107.7 ?
C11 C12 H12B . . 107.7 ?
H12A C12 H12B . . 107.1 ?
C1 C12a C4a . . 118.0(2) ?
C1 C12a C12 . . 118.7(2) ?
C4a C12a C12 . . 123.3(2) ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
O51 C51 N5 . . 121.5(2) ?
O51 C51 C52 . . 121.4(2) ?
N5 C51 C52 . . 117.1(2) ?
C51 C52 H52A . . 109.5 ?
C51 C52 H52B . . 109.5 ?
H52A C52 H52B . . 109.5 ?
C51 C52 H52C . . 109.5 ?
H52A C52 H52C . . 109.5 ?
H52B C52 H52C . . 109.5 ?
C8 C81 H81A . . 109.5 ?
C8 C81 H81B . . 109.5 ?
H81A C81 H81B . . 109.5 ?
C8 C81 H81C . . 109.5 ?
H81A C81 H81C . . 109.5 ?
H81B C81 H81C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.385(3) ?
C1 C12a . 1.396(3) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.382(4) ?
C2 Cl1 . 1.745(2) ?
C3 C4 . 1.386(3) ?
C3 H3 . 0.9500 ?
C4 C4a . 1.389(3) ?
C4 H4 . 0.9500 ?
C4a C12a . 1.398(3) ?
C4a N5 . 1.437(3) ?
N5 C51 . 1.362(3) ?
N5 C6 . 1.484(3) ?
C6 C6a . 1.514(4) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C6a C10a . 1.391(3) ?
C6a C7 . 1.395(4) ?
C7 C8 . 1.402(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.396(4) ?
C8 C81 . 1.499(4) ?
C9 C10 . 1.384(4) ?
C9 H9 . 0.9500 ?
C10 C10a . 1.392(4) ?
C10 H10 . 0.9500 ?
C10a C11 . 1.524(4) ?
C11 C13 . 1.528(4) ?
C11 C12 . 1.539(3) ?
C11 H11 . 1.0000 ?
C12 C12a . 1.515(3) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
O51 C51 . 1.227(3) ?
C51 C52 . 1.500(4) ?
C52 H52A . 0.9800 ?
C52 H52B . 0.9800 ?
C52 H52C . 0.9800 ?
C81 H81A . 0.9800 ?
C81 H81B . 0.9800 ?
C81 H81C . 0.9800 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12a C1 C2 C3 . . . . 1.5(4) ?
C12a C1 C2 Cl1 . . . . -178.65(19) ?
C1 C2 C3 C4 . . . . -0.7(4) ?
Cl1 C2 C3 C4 . . . . 179.48(19) ?
C2 C3 C4 C4a . . . . -1.3(4) ?
C3 C4 C4a C12a . . . . 2.5(4) ?
C3 C4 C4a N5 . . . . -177.8(2) ?
C4 C4a N5 C51 . . . . 86.4(3) ?
C12a C4a N5 C51 . . . . -93.9(3) ?
C4 C4a N5 C6 . . . . -87.8(3) ?
C12a C4a N5 C6 . . . . 91.9(3) ?
C51 N5 C6 C6a . . . . 146.7(2) ?
C4a N5 C6 C6a . . . . -38.9(3) ?
N5 C6 C6a C10a . . . . -46.9(3) ?
N5 C6 C6a C7 . . . . 137.8(2) ?
C10a C6a C7 C8 . . . . 1.2(4) ?
C6 C6a C7 C8 . . . . 176.7(2) ?
C6a C7 C8 C9 . . . . 1.8(4) ?
C6a C7 C8 C81 . . . . -175.9(2) ?
C7 C8 C9 C10 . . . . -2.6(4) ?
C81 C8 C9 C10 . . . . 175.1(3) ?
C8 C9 C10 C10a . . . . 0.4(4) ?
C7 C6a C10a C10 . . . . -3.5(4) ?
C6 C6a C10a C10 . . . . -178.6(2) ?
C7 C6a C10a C11 . . . . 176.4(2) ?
C6 C6a C10a C11 . . . . 1.2(4) ?
C9 C10 C10a C6a . . . . 2.7(4) ?
C9 C10 C10a C11 . . . . -177.1(2) ?
C6a C10a C11 C13 . . . . -144.9(2) ?
C10 C10a C11 C13 . . . . 34.9(3) ?
C6a C10a C11 C12 . . . . 92.0(3) ?
C10 C10a C11 C12 . . . . -88.2(3) ?
C10a C11 C12 C12a . . . . -42.5(3) ?
C13 C11 C12 C12a . . . . -168.4(2) ?
C2 C1 C12a C4a . . . . -0.3(4) ?
C2 C1 C12a C12 . . . . 178.1(2) ?
C4 C4a C12a C1 . . . . -1.7(3) ?
N5 C4a C12a C1 . . . . 178.6(2) ?
C4 C4a C12a C12 . . . . 180.0(2) ?
N5 C4a C12a C12 . . . . 0.3(3) ?
C11 C12 C12a C1 . . . . 142.8(2) ?
C11 C12 C12a C4a . . . . -38.9(4) ?
C4a N5 C51 O51 . . . . -176.8(2) ?
C6 N5 C51 O51 . . . . -2.6(3) ?
C4a N5 C51 C52 . . . . 4.1(3) ?
C6 N5 C51 C52 . . . . 178.3(2) ?
