#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:37:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178434 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/55/4025569.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_4025569
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         'C25 H21 N O3'
_chemical_formula_sum            'C25 H21 N O3'
_chemical_formula_weight         383.43
_chemical_melting_point          153
_chemical_name_systematic
;
Methyl (3RS,13bRS)-2-methyl-3-phenyl-3,13b-dihydrodibenzo[b,f]
pyrrolo[1,2-d][1,4]oxazepine-1-carboxylate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.23(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8716(5)
_cell_length_b                   15.0615(6)
_cell_length_c                   10.6577(4)
_cell_measurement_reflns_used    1713
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.203
_cell_measurement_theta_min      2.351
_cell_volume                     1890.49(16)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_diffrn_ambient_temperature      120.15
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       /w-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.1200
_diffrn_reflns_av_sigmaI/netI    0.1343
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15089
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.73
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2006/1 (Bruker,2006) was used for absorption correction.
 R(int) was 0.0564 before and 0.0418 after correction.
 The Ratio of minimum to maximum transmission is 0.037.
 The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            less
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1542
_refine_ls_R_factor_gt           0.0568
_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)+(0.0200P)²+0.0000P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1310
_reflns_number_gt                2035
_reflns_number_total             4331
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100966j_si_005.cif
_cod_data_source_block           SAD_14B
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_cell_volume        1890.49(14)
_cod_database_code               4025569
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_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
O7 O 0.91487(17) 0.52826(12) 0.78992(17) 0.0287(5) Uani 1 1 d . . .
O27 O 0.74323(18) 0.69258(12) 0.43233(17) 0.0334(5) Uani 1 1 d . . .
O28 O 0.69818(18) 0.63336(12) 0.23874(18) 0.0319(5) Uani 1 1 d . . .
N1 N 0.8708(2) 0.43942(14) 0.5438(2) 0.0254(6) Uani 1 1 d . . .
C1 C 0.9501(2) 0.44080(17) 0.7687(3) 0.0259(7) Uani 1 1 d . . .
C2 C 0.9296(2) 0.39905(18) 0.6491(3) 0.0251(6) Uani 1 1 d . . .
C4 C 0.8283(3) 0.53085(18) 0.5408(3) 0.0246(6) Uani 1 1 d . . .
C5 C 0.7493(3) 0.54430(16) 0.6387(2) 0.0238(6) Uani 1 1 d . . .
C6 C 0.7973(3) 0.54173(16) 0.7646(3) 0.0251(7) Uani 1 1 d . . .
C8 C 1.0114(3) 0.39852(19) 0.8704(3) 0.0304(7) Uani 1 1 d . . .
C9 C 1.0556(3) 0.31455(19) 0.8590(3) 0.0316(7) Uani 1 1 d . . .
C10 C 1.0341(3) 0.27156(19) 0.7437(3) 0.0290(7) Uani 1 1 d . . .
C11 C 0.9725(2) 0.31314(18) 0.6413(3) 0.0260(6) Uani 1 1 d . . .
C12 C 0.6316(3) 0.55561(17) 0.6147(3) 0.0268(7) Uani 1 1 d . . .
C13 C 0.5675(3) 0.56736(19) 0.7128(3) 0.0326(7) Uani 1 1 d . . .
C14 C 0.6185(3) 0.56780(19) 0.8373(3) 0.0346(8) Uani 1 1 d . . .
C15 C 0.7349(3) 0.55516(18) 0.8641(3) 0.0325(8) Uani 1 1 d . . .
C16 C 0.8376(3) 0.39238(18) 0.4256(3) 0.0253(7) Uani 1 1 d . . .
C17 C 0.7859(2) 0.46566(17) 0.3395(3) 0.0253(6) Uani 1 1 d . . .
C18 C 0.7791(2) 0.54045(17) 0.4042(2) 0.0242(6) Uani 1 1 d . . .
C19 C 0.7546(2) 0.31600(17) 0.4344(2) 0.0256(6) Uani 1 1 d . . .
C20 C 0.6727(3) 0.31981(19) 0.5166(3) 0.0277(7) Uani 1 1 d . . .
C21 C 0.5965(3) 0.2506(2) 0.5229(3) 0.0340(8) Uani 1 1 d . . .
C22 C 0.5996(3) 0.17790(19) 0.4440(3) 0.0317(7) Uani 1 1 d . . .
C23 C 0.6801(3) 0.17418(19) 0.3613(3) 0.0307(7) Uani 1 1 d . . .
C24 C 0.7572(3) 0.24252(18) 0.3548(3) 0.0294(7) Uani 1 1 d . . .
C25 C 0.7546(3) 0.4450(2) 0.2016(3) 0.0335(8) Uani 1 1 d . . .
C26 C 0.7384(3) 0.62946(18) 0.3616(3) 0.0271(7) Uani 1 1 d . . .
C29 C 0.6649(3) 0.7216(2) 0.1939(3) 0.0347(8) Uani 1 1 d . . .
H4 H 0.900(2) 0.5783(16) 0.559(2) 0.023(7) Uiso 1 1 d . . .
H8 H 1.022(3) 0.435(2) 0.950(3) 0.056(10) Uiso 1 1 d . . .
H9 H 1.102(3) 0.283(2) 0.930(3) 0.048(10) Uiso 1 1 d . . .
H10 H 1.065(2) 0.2121(19) 0.730(3) 0.035(8) Uiso 1 1 d . . .
H11 H 0.960(2) 0.2810(18) 0.561(3) 0.033(8) Uiso 1 1 d . . .
H12 H 0.597(3) 0.5560(18) 0.530(3) 0.036(9) Uiso 1 1 d . . .
H13 H 0.482(2) 0.5778(17) 0.693(2) 0.026(8) Uiso 1 1 d . . .
H14 H 0.576(2) 0.5793(15) 0.906(2) 0.012(6) Uiso 1 1 d . . .
H15 H 0.773(3) 0.5545(19) 0.948(3) 0.045(10) Uiso 1 1 d . . .
H16 H 0.906(3) 0.3696(17) 0.393(2) 0.030(8) Uiso 1 1 d . . .
H20 H 0.670(2) 0.3672(18) 0.569(3) 0.031(8) Uiso 1 1 d . . .
H21 H 0.538(2) 0.2576(17) 0.577(3) 0.027(8) Uiso 1 1 d . . .
H22 H 0.535(3) 0.1309(19) 0.444(3) 0.045(9) Uiso 1 1 d . . .
H23 H 0.682(2) 0.1219(18) 0.303(2) 0.032(8) Uiso 1 1 d . . .
H24 H 0.808(2) 0.2429(17) 0.295(2) 0.026(8) Uiso 1 1 d . . .
H251 H 0.827(3) 0.427(2) 0.170(3) 0.053(10) Uiso 1 1 d . . .
H252 H 0.707(3) 0.4965(19) 0.154(3) 0.035(8) Uiso 1 1 d . . .
H253 H 0.706(3) 0.387(2) 0.195(3) 0.067(11) Uiso 1 1 d . . .
H291 H 0.723(2) 0.7725(18) 0.232(2) 0.033(8) Uiso 1 1 d . . .
H292 H 0.588(3) 0.740(2) 0.223(3) 0.074(12) Uiso 1 1 d . . .
H293 H 0.657(3) 0.714(2) 0.100(3) 0.064(11) 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'
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
C6 O7 C1 114.4(2) . . ?
C26 O28 C29 114.3(2) . . ?
C2 N1 C16 122.8(2) . . ?
C2 N1 C4 124.6(2) . . ?
C16 N1 C4 112.5(2) . . ?
C8 C1 O7 116.3(2) . . ?
C8 C1 C2 121.0(3) . . ?
O7 C1 C2 122.6(2) . . ?
N1 C2 C11 120.6(2) . . ?
N1 C2 C1 123.1(2) . . ?
C11 C2 C1 116.3(3) . . ?
N1 C4 C5 110.8(2) . . ?
N1 C4 C18 101.7(2) . . ?
C5 C4 C18 117.3(2) . . ?
N1 C4 H4 110.2(13) . . ?
C5 C4 H4 109.1(13) . . ?
C18 C4 H4 107.5(13) . . ?
C6 C5 C12 117.3(3) . . ?
C6 C5 C4 116.8(3) . . ?
C12 C5 C4 125.9(3) . . ?
C15 C6 C5 122.8(3) . . ?
C15 C6 O7 119.3(3) . . ?
C5 C6 O7 117.9(2) . . ?
C9 C8 C1 121.4(3) . . ?
C9 C8 H8 124.9(18) . . ?
C1 C8 H8 113.7(18) . . ?
C8 C9 C10 118.5(3) . . ?
C8 C9 H9 122.9(18) . . ?
C10 C9 H9 118.6(18) . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10 121.9(16) . . ?
C11 C10 H10 117.5(16) . . ?
C10 C11 C2 122.1(3) . . ?
C10 C11 H11 118.2(16) . . ?
C2 C11 H11 119.7(16) . . ?
C13 C12 C5 120.7(3) . . ?
C13 C12 H12 120.8(19) . . ?
C5 C12 H12 118.5(19) . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.2(15) . . ?
C14 C13 H13 120.2(15) . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 121.4(15) . . ?
C15 C14 H14 118.6(14) . . ?
C6 C15 C14 118.5(3) . . ?
C6 C15 H15 119(2) . . ?
C14 C15 H15 122(2) . . ?
N1 C16 C17 102.4(2) . . ?
N1 C16 C19 114.9(2) . . ?
C17 C16 C19 111.8(2) . . ?
N1 C16 H16 108.9(16) . . ?
C17 C16 H16 109.4(15) . . ?
C19 C16 H16 109.2(16) . . ?
C18 C17 C25 131.3(3) . . ?
C18 C17 C16 110.5(2) . . ?
C25 C17 C16 118.2(2) . . ?
C17 C18 C26 130.5(3) . . ?
C17 C18 C4 112.3(2) . . ?
C26 C18 C4 117.2(2) . . ?
C20 C19 C24 119.1(3) . . ?
C20 C19 C16 121.1(2) . . ?
C24 C19 C16 119.8(3) . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.0(18) . . ?
C19 C20 H20 120.2(18) . . ?
C20 C21 C22 119.9(3) . . ?
C20 C21 H21 118.0(16) . . ?
C22 C21 H21 121.9(16) . . ?
C23 C22 C21 119.6(3) . . ?
C23 C22 H22 122.8(16) . . ?
C21 C22 H22 117.4(17) . . ?
C22 C23 C24 121.1(3) . . ?
C22 C23 H23 119.6(16) . . ?
C24 C23 H23 119.3(16) . . ?
C23 C24 C19 119.6(3) . . ?
C23 C24 H24 121.7(16) . . ?
C19 C24 H24 118.6(16) . . ?
C17 C25 H251 105.7(19) . . ?
C17 C25 H252 111.8(15) . . ?
H251 C25 H252 118(2) . . ?
C17 C25 H253 108.1(18) . . ?
H251 C25 H253 104(3) . . ?
H252 C25 H253 109(3) . . ?
O27 C26 O28 123.9(2) . . ?
O27 C26 C18 122.3(2) . . ?
O28 C26 C18 113.8(2) . . ?
O28 C29 H291 113.1(15) . . ?
O28 C29 H292 111(2) . . ?
H291 C29 H292 104(2) . . ?
O28 C29 H293 102.3(19) . . ?
H291 C29 H293 116(2) . . ?
H292 C29 H293 111(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
O7 C6 1.402(4) . ?
O7 C1 1.409(3) . ?
O27 C26 1.210(3) . ?
O28 C26 1.338(3) . ?
O28 C29 1.450(3) . ?
N1 C2 1.385(3) . ?
N1 C16 1.456(3) . ?
N1 C4 1.466(3) . ?
C1 C8 1.383(4) . ?
C1 C2 1.414(4) . ?
C2 C11 1.397(4) . ?
C4 C5 1.503(4) . ?
C4 C18 1.505(4) . ?
C4 H4 1.11(3) . ?
C5 C6 1.391(4) . ?
C5 C12 1.398(4) . ?
C6 C15 1.383(4) . ?
C8 C9 1.380(4) . ?
C8 H8 1.01(3) . ?
C9 C10 1.384(4) . ?
C9 H9 1.00(3) . ?
C10 C11 1.385(4) . ?
C10 H10 0.98(3) . ?
C11 H11 0.98(3) . ?
C12 C13 1.380(4) . ?
C12 H12 0.94(3) . ?
C13 C14 1.387(4) . ?
C13 H13 1.02(3) . ?
C14 C15 1.389(5) . ?
C14 H14 0.96(2) . ?
C15 H15 0.95(3) . ?
C16 C17 1.515(4) . ?
C16 C19 1.525(4) . ?
C16 H16 0.99(3) . ?
C17 C18 1.329(4) . ?
C17 C25 1.502(4) . ?
C18 C26 1.477(4) . ?
C19 C20 1.390(4) . ?
C19 C24 1.397(4) . ?
C20 C21 1.387(4) . ?
C20 H20 0.91(3) . ?
C21 C22 1.384(4) . ?
C21 H21 0.96(3) . ?
C22 C23 1.381(4) . ?
C22 H22 1.04(3) . ?
C23 C24 1.385(4) . ?
C23 H23 1.00(3) . ?
C24 H24 0.93(3) . ?
C25 H251 0.99(4) . ?
C25 H252 1.05(3) . ?
C25 H253 1.05(4) . ?
C29 H291 1.08(3) . ?
C29 H292 1.04(4) . ?
C29 H293 1.00(3) . ?
