#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:37:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178434 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/55/4025570.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_4025570
loop_
_publ_author_name
'Alexander F. Khlebnikov'
'Mikhail S. Novikov'
'Petr P. Petrovskii'
'Alexander S. Konev'
'Dmitrii S. Yufit'
'Stanislav I. Selivanov'
'Holm Frauendorf'
_publ_contact_author_address
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;
_publ_contact_author_email       d.s.yufit@durham.ac.uk
_publ_contact_author_fax         '0191 384 4737'
_publ_contact_author_name        'Dmitry Yufit'
_publ_contact_author_phone       '0191 334 2004'
_publ_section_title
;
 Stereoselective Cycloaddition of Dibenzoxazepinium Ylides to Acetylenes
 and Fullerene C60. Conformational Behavior of
 3-Aryldibenzo[b,f]pyrrolo[1,2-d][1,4]oxazepine Systems
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5211
_journal_page_last               5215
_journal_paper_doi               10.1021/jo100966j
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C24 H19 N O3'
_chemical_formula_sum            'C24 H19 N O3'
_chemical_formula_weight         369.40
_chemical_melting_point          204
_chemical_name_systematic
;
Methyl (3RS,13bRS)-3-phenyl-3,13b-dihydrodibenzo[b,f]pyrrolo[1,2-d]
[1,4]oxazepine-2-carboxylate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                115.75(2)
_cell_angle_beta                 113.51(2)
_cell_angle_gamma                94.86(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2576(2)
_cell_length_b                   11.0167(2)
_cell_length_c                   11.0998(2)
_cell_measurement_reflns_used    4383
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.373
_cell_measurement_theta_min      2.16
_cell_volume                     888.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
Olex2, Durham University (compiled Mar 6 2009 16:11:20)
;
_computing_publication_material
;
Olex2, Durham University (compiled Mar 6 2009 16:11:20)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11429
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.16
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.4033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2006/1 (Bruker,2006) was used for absorption correction.
 R(int) was 0.0435 before and 0.0249 after correction.
 The Ratio of minimum to maximum transmission is 0.4033.
 The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0517
_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)+(0.0600P)²+1.2000P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1555
_reflns_number_gt                3363
_reflns_number_total             4242
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100966j_si_006.cif
_cod_data_source_block           SAD_15A
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025570
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
O3 O 0.84588(19) 0.02124(15) 0.17430(17) 0.0262(3) Uani 1 1 d . . .
O26 O 1.2788(2) -0.39078(17) 0.44293(17) 0.0293(3) Uani 1 1 d . . .
O27 O 1.36046(18) -0.39525(17) 0.27555(18) 0.0273(3) Uani 1 1 d . . .
N3 N 0.9465(2) -0.18809(18) 0.2615(2) 0.0227(4) Uani 1 1 d . . .
C1 C 0.7800(2) -0.0286(2) 0.2438(2) 0.0219(4) Uani 1 1 d . . .
C2 C 0.8346(2) -0.1237(2) 0.2927(2) 0.0210(4) Uani 1 1 d . . .
C4 C 1.0487(2) -0.1427(2) 0.2065(2) 0.0216(4) Uani 1 1 d . . .
C5 C 0.9443(2) -0.1637(2) 0.0495(2) 0.0219(4) Uani 1 1 d . . .
C6 C 0.8426(3) -0.0785(2) 0.0410(2) 0.0237(4) Uani 1 1 d . . .
C8 C 0.6632(3) 0.0306(2) 0.2727(2) 0.0249(4) Uani 1 1 d . . .
C9 C 0.5946(3) -0.0013(2) 0.3504(2) 0.0260(4) Uani 1 1 d . . .
C10 C 0.6468(3) -0.0932(2) 0.4000(2) 0.0246(4) Uani 1 1 d . . .
C11 C 0.7640(2) -0.1526(2) 0.3720(2) 0.0230(4) Uani 1 1 d . . .
C12 C 0.9488(3) -0.2562(2) -0.0822(2) 0.0248(4) Uani 1 1 d . . .
C13 C 0.8543(3) -0.2605(2) -0.2189(2) 0.0282(4) Uani 1 1 d . . .
C14 C 0.7546(3) -0.1738(2) -0.2242(3) 0.0292(5) Uani 1 1 d . . .
C15 C 0.7478(3) -0.0816(2) -0.0938(3) 0.0269(4) Uani 1 1 d . . .
C16 C 1.0095(2) -0.2786(2) 0.3220(2) 0.0202(4) Uani 1 1 d . . .
C17 C 1.1518(2) -0.2943(2) 0.2884(2) 0.0217(4) Uani 1 1 d . . .
C18 C 1.1684(2) -0.2245(2) 0.2199(2) 0.0226(4) Uani 1 1 d . . .
C19 C 0.8805(2) -0.4213(2) 0.2454(2) 0.0207(4) Uani 1 1 d . . .
C20 C 1.2671(2) -0.3665(2) 0.3440(2) 0.0222(4) Uani 1 1 d . . .
C21 C 0.7583(3) -0.4884(2) 0.0926(2) 0.0240(4) Uani 1 1 d . . .
C22 C 0.6446(3) -0.6200(2) 0.0245(2) 0.0267(4) Uani 1 1 d . . .
C23 C 0.6529(3) -0.6863(2) 0.1071(3) 0.0283(4) Uani 1 1 d . . .
C24 C 0.7735(3) -0.6202(2) 0.2594(3) 0.0295(5) Uani 1 1 d . . .
C25 C 0.8857(3) -0.4879(2) 0.3281(2) 0.0256(4) Uani 1 1 d . . .
C28 C 1.4834(3) -0.4600(3) 0.3251(3) 0.0316(5) Uani 1 1 d . . .
H4 H 1.112(3) -0.039(3) 0.276(3) 0.020(6) Uiso 1 1 d . . .
H8 H 0.636(3) 0.099(3) 0.240(3) 0.028(6) Uiso 1 1 d . . .
H9 H 0.511(3) 0.041(3) 0.371(3) 0.027(6) Uiso 1 1 d . . .
H10 H 0.599(3) -0.114(3) 0.455(3) 0.027(6) Uiso 1 1 d . . .
H11 H 0.803(3) -0.219(3) 0.412(3) 0.023(6) Uiso 1 1 d . . .
H12 H 1.021(3) -0.318(3) -0.078(3) 0.026(6) Uiso 1 1 d . . .
H13 H 0.861(3) -0.326(3) -0.309(3) 0.034(7) Uiso 1 1 d . . .
H14 H 0.686(3) -0.182(3) -0.322(3) 0.029(6) Uiso 1 1 d . . .
H15 H 0.679(3) -0.021(3) -0.092(3) 0.027(6) Uiso 1 1 d . . .
H16 H 1.050(3) -0.230(3) 0.433(3) 0.021(6) Uiso 1 1 d . . .
H18 H 1.252(3) -0.219(3) 0.186(3) 0.029(6) Uiso 1 1 d . . .
H21 H 0.752(3) -0.442(3) 0.033(3) 0.028(6) Uiso 1 1 d . . .
H22 H 0.562(4) -0.666(3) -0.077(3) 0.040(8) Uiso 1 1 d . . .
H23 H 0.572(3) -0.779(3) 0.058(3) 0.030(7) Uiso 1 1 d . . .
H24 H 0.780(3) -0.665(3) 0.320(3) 0.037(7) Uiso 1 1 d . . .
H25 H 0.968(4) -0.436(3) 0.433(3) 0.036(7) Uiso 1 1 d . . .
H281 H 1.429(4) -0.557(3) 0.290(3) 0.043(8) Uiso 1 1 d . . .
H282 H 1.547(4) -0.410(4) 0.437(4) 0.061(10) Uiso 1 1 d . . .
H283 H 1.553(4) -0.459(3) 0.276(3) 0.040(8) Uiso 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'
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'
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
C6 O3 C1 117.90(15) . . ?
C20 O27 C28 116.76(17) . . ?
C2 N3 C16 121.70(16) . . ?
C2 N3 C4 123.60(17) . . ?
C16 N3 C4 112.43(15) . . ?
C8 C1 O3 114.44(18) . . ?
C8 C1 C2 121.27(19) . . ?
O3 C1 C2 124.12(18) . . ?
N3 C2 C11 121.10(18) . . ?
N3 C2 C1 122.75(18) . . ?
C11 C2 C1 116.12(18) . . ?
N3 C4 C18 102.52(16) . . ?
N3 C4 C5 111.94(16) . . ?
C18 C4 C5 116.76(17) . . ?
N3 C4 H4 111.0(13) . . ?
C18 C4 H4 108.7(13) . . ?
C5 C4 H4 105.9(13) . . ?
C6 C5 C12 118.90(19) . . ?
C6 C5 C4 116.12(18) . . ?
C12 C5 C4 124.92(18) . . ?
C15 C6 C5 121.9(2) . . ?
C15 C6 O3 118.62(19) . . ?
C5 C6 O3 119.26(18) . . ?
C1 C8 C9 121.1(2) . . ?
C1 C8 H8 116.7(15) . . ?
C9 C8 H8 122.1(15) . . ?
C10 C9 C8 118.57(19) . . ?
C10 C9 H9 120.3(15) . . ?
C8 C9 H9 121.1(15) . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 H10 121.4(15) . . ?
C9 C10 H10 118.0(15) . . ?
C10 C11 C2 122.3(2) . . ?
C10 C11 H11 118.9(13) . . ?
C2 C11 H11 118.8(13) . . ?
C5 C12 C13 120.0(2) . . ?
C5 C12 H12 120.2(14) . . ?
C13 C12 H12 119.8(14) . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 122.1(16) . . ?
C12 C13 H13 117.9(16) . . ?
C13 C14 C15 120.7(2) . . ?
C13 C14 H14 118.6(15) . . ?
C15 C14 H14 120.7(15) . . ?
C6 C15 C14 118.5(2) . . ?
C6 C15 H15 117.3(15) . . ?
C14 C15 H15 124.2(15) . . ?
N3 C16 C17 101.26(15) . . ?
N3 C16 C19 113.24(16) . . ?
C17 C16 C19 112.34(16) . . ?
N3 C16 H16 110.7(14) . . ?
C17 C16 H16 110.4(14) . . ?
C19 C16 H16 108.8(14) . . ?
C18 C17 C20 125.90(18) . . ?
C18 C17 C16 112.19(17) . . ?
C20 C17 C16 121.55(17) . . ?
C17 C18 C4 111.18(18) . . ?
C17 C18 H18 127.3(15) . . ?
C4 C18 H18 121.4(15) . . ?
C21 C19 C25 118.81(19) . . ?
C21 C19 C16 121.39(18) . . ?
C25 C19 C16 119.79(17) . . ?
O26 C20 O27 124.69(18) . . ?
O26 C20 C17 123.77(18) . . ?
O27 C20 C17 111.49(17) . . ?
C22 C21 C19 120.23(19) . . ?
C22 C21 H21 119.9(15) . . ?
C19 C21 H21 119.8(15) . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 118.3(18) . . ?
C21 C22 H22 121.3(18) . . ?
C22 C23 C24 119.8(2) . . ?
C22 C23 H23 119.6(15) . . ?
C24 C23 H23 120.6(15) . . ?
C23 C24 C25 119.8(2) . . ?
C23 C24 H24 121.0(16) . . ?
C25 C24 H24 119.1(16) . . ?
C24 C25 C19 120.9(2) . . ?
C24 C25 H25 123.6(17) . . ?
C19 C25 H25 115.5(17) . . ?
O27 C28 H281 109.6(18) . . ?
O27 C28 H282 111(2) . . ?
H281 C28 H282 107(3) . . ?
O27 C28 H283 105.9(17) . . ?
H281 C28 H283 110(2) . . ?
H282 C28 H283 114(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
O3 C6 1.394(3) . ?
O3 C1 1.398(2) . ?
O26 C20 1.206(2) . ?
O27 C20 1.336(2) . ?
O27 C28 1.445(3) . ?
N3 C2 1.376(3) . ?
N3 C16 1.468(2) . ?
N3 C4 1.471(2) . ?
C1 C8 1.383(3) . ?
C1 C2 1.418(3) . ?
C2 C11 1.403(3) . ?
C4 C18 1.489(3) . ?
C4 C5 1.514(3) . ?
C4 H4 1.00(2) . ?
C5 C6 1.390(3) . ?
C5 C12 1.393(3) . ?
C6 C15 1.384(3) . ?
C8 C9 1.391(3) . ?
C8 H8 0.98(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.98(3) . ?
C10 C11 1.383(3) . ?
C10 H10 0.97(3) . ?
C11 H11 1.04(2) . ?
C12 C13 1.393(3) . ?
C12 H12 0.99(3) . ?
C13 C14 1.387(3) . ?
C13 H13 0.98(3) . ?
C14 C15 1.391(3) . ?
C14 H14 0.97(3) . ?
C15 H15 0.96(3) . ?
C16 C17 1.509(3) . ?
C16 C19 1.526(3) . ?
C16 H16 0.98(2) . ?
C17 C18 1.333(3) . ?
C17 C20 1.483(3) . ?
C18 H18 0.99(3) . ?
C19 C21 1.393(3) . ?
C19 C25 1.393(3) . ?
C21 C22 1.391(3) . ?
C21 H21 0.99(3) . ?
C22 C23 1.384(3) . ?
C22 H22 0.93(3) . ?
C23 C24 1.386(3) . ?
C23 H23 0.98(3) . ?
C24 C25 1.389(3) . ?
C24 H24 0.98(3) . ?
C25 H25 0.95(3) . ?
C28 H281 0.97(3) . ?
C28 H282 0.98(4) . ?
C28 H283 0.99(3) . ?
