#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:37:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178434 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/55/4025571.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_4025571
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         'C30 H23 N O3'
_chemical_formula_sum            'C30 H23 N O3'
_chemical_formula_weight         445.49
_chemical_melting_point          195
_chemical_name_systematic
;
Methyl (3RS,13bRS)-1,3-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                108.927(10)
_cell_angle_beta                 98.385(10)
_cell_angle_gamma                107.894(10)
_cell_formula_units_Z            2
_cell_length_a                   8.8961(2)
_cell_length_b                   10.4555(3)
_cell_length_c                   13.7527(4)
_cell_measurement_reflns_used    5755
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.477
_cell_measurement_theta_min      2.182
_cell_volume                     1107.84(15)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0302
_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       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13759
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.18
_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    0.086
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.4755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2006/1 (Bruker,2006) was used for absorption correction.
 R(int) was 0.0479 before and 0.0250 after correction.
 The Ratio of minimum to maximum transmission is 0.4755.
 The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0468
_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)+(0.0900P)²+0.1900P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1442
_reflns_number_gt                4724
_reflns_number_total             5867
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100966j_si_007.cif
_cod_data_source_block           SAD_15c
_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_original_cell_volume        1107.8(1)
_cod_database_code               4025571
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
O7 O 0.84045(11) 0.78928(10) 0.24446(8) 0.0251(2) Uani 1 1 d . . .
O32 O 1.02859(12) 1.49682(10) 0.21554(8) 0.0317(2) Uani 1 1 d . . .
O33 O 0.80945(12) 1.34203(10) 0.07743(8) 0.0296(2) Uani 1 1 d . . .
N3 N 0.79467(12) 1.04984(11) 0.23104(8) 0.0206(2) Uani 1 1 d . . .
C1 C 0.69603(15) 0.81488(13) 0.24998(10) 0.0219(2) Uani 1 1 d . . .
C2 C 0.67246(14) 0.93876(13) 0.24118(9) 0.0199(2) Uani 1 1 d . . .
C4 C 0.94103(14) 1.03342(12) 0.20070(9) 0.0183(2) Uani 1 1 d . . .
C5 C 1.05116(15) 1.02394(13) 0.29095(9) 0.0199(2) Uani 1 1 d . . .
C6 C 0.98729(15) 0.90034(13) 0.31313(10) 0.0225(2) Uani 1 1 d . . .
C8 C 0.57123(17) 0.70576(14) 0.25981(11) 0.0267(3) Uani 1 1 d . . .
C9 C 0.41926(17) 0.71457(15) 0.26213(11) 0.0298(3) Uani 1 1 d . . .
C10 C 0.39394(16) 0.83634(15) 0.25520(11) 0.0277(3) Uani 1 1 d . . .
C11 C 0.51863(15) 0.94657(14) 0.24534(10) 0.0233(2) Uani 1 1 d . . .
C12 C 1.20341(16) 1.12971(14) 0.35545(10) 0.0240(3) Uani 1 1 d . . .
C13 C 1.28934(17) 1.11136(15) 0.44005(11) 0.0289(3) Uani 1 1 d . . .
C14 C 1.22212(19) 0.98791(17) 0.46109(11) 0.0307(3) Uani 1 1 d . . .
C15 C 1.07027(17) 0.88129(16) 0.39759(11) 0.0281(3) Uani 1 1 d . . .
C16 C 0.76855(14) 1.17642(12) 0.22177(9) 0.0189(2) Uani 1 1 d . . .
C17 C 0.91605(14) 1.24278(12) 0.18597(9) 0.0188(2) Uani 1 1 d . . .
C18 C 1.01123(14) 1.16414(12) 0.17281(9) 0.0185(2) Uani 1 1 d . . .
C19 C 0.75602(14) 1.28049(13) 0.32495(10) 0.0206(2) Uani 1 1 d . . .
C20 C 0.92908(14) 1.37549(13) 0.16344(9) 0.0201(2) Uani 1 1 d . . .
C21 C 1.15157(14) 1.17889(13) 0.12616(9) 0.0191(2) Uani 1 1 d . . .
C22 C 0.83898(17) 1.29323(14) 0.42346(10) 0.0261(3) Uani 1 1 d . . .
C23 C 0.8254(2) 1.38654(16) 0.51760(11) 0.0326(3) Uani 1 1 d . . .
C24 C 0.7311(2) 1.46834(16) 0.51321(12) 0.0345(3) Uani 1 1 d . . .
C25 C 0.6497(2) 1.45795(18) 0.41539(13) 0.0382(3) Uani 1 1 d . . .
C26 C 0.66062(18) 1.36301(16) 0.32106(11) 0.0305(3) Uani 1 1 d . . .
C27 C 1.23367(16) 1.30397(14) 0.10866(11) 0.0243(3) Uani 1 1 d . . .
C28 C 1.35844(16) 1.30954(15) 0.05855(11) 0.0270(3) Uani 1 1 d . . .
C29 C 1.40621(15) 1.19117(15) 0.02505(10) 0.0249(3) Uani 1 1 d . . .
C30 C 1.32948(15) 1.06825(14) 0.04430(10) 0.0237(3) Uani 1 1 d . . .
C31 C 1.20367(15) 1.06173(13) 0.09383(9) 0.0215(2) Uani 1 1 d . . .
C34 C 0.7999(2) 1.46466(17) 0.05268(13) 0.0342(3) Uani 1 1 d . . .
H4 H 0.9051(19) 0.9414(17) 0.1369(13) 0.023(4) Uiso 1 1 d . . .
H8 H 0.598(2) 0.625(2) 0.2687(14) 0.035(4) Uiso 1 1 d . . .
H9 H 0.327(2) 0.639(2) 0.2700(15) 0.041(5) Uiso 1 1 d . . .
H10 H 0.289(2) 0.8428(18) 0.2579(13) 0.029(4) Uiso 1 1 d . . .
H11 H 0.4960(19) 1.0317(17) 0.2400(13) 0.024(4) Uiso 1 1 d . . .
H12 H 1.250(2) 1.2148(18) 0.3392(13) 0.024(4) Uiso 1 1 d . . .
H13 H 1.395(2) 1.1843(19) 0.4840(14) 0.031(4) Uiso 1 1 d . . .
H14 H 1.278(2) 0.977(2) 0.5206(15) 0.041(5) Uiso 1 1 d . . .
H15 H 1.021(2) 0.796(2) 0.4120(14) 0.033(4) Uiso 1 1 d . . .
H16 H 0.6688(19) 1.1512(17) 0.1648(12) 0.021(4) Uiso 1 1 d . . .
H22 H 0.906(2) 1.2352(19) 0.4247(14) 0.032(4) Uiso 1 1 d . . .
H23 H 0.886(2) 1.398(2) 0.5899(16) 0.045(5) Uiso 1 1 d . . .
H24 H 0.722(2) 1.538(2) 0.5814(15) 0.044(5) Uiso 1 1 d . . .
H25 H 0.582(2) 1.518(2) 0.4121(16) 0.044(5) Uiso 1 1 d . . .
H26 H 0.602(2) 1.351(2) 0.2476(15) 0.039(5) Uiso 1 1 d . . .
H27 H 1.202(2) 1.3849(19) 0.1299(14) 0.033(4) Uiso 1 1 d . . .
H28 H 1.414(2) 1.398(2) 0.0467(15) 0.040(5) Uiso 1 1 d . . .
H29 H 1.492(2) 1.1916(18) -0.0117(14) 0.030(4) Uiso 1 1 d . . .
H30 H 1.3621(19) 0.9839(18) 0.0212(12) 0.023(4) Uiso 1 1 d . . .
H31 H 1.152(2) 0.9726(18) 0.1061(13) 0.026(4) Uiso 1 1 d . . .
H341 H 0.758(2) 1.526(2) 0.1061(15) 0.040(5) Uiso 1 1 d . . .
H342 H 0.902(3) 1.520(2) 0.0476(17) 0.052(6) Uiso 1 1 d . . .
H343 H 0.722(2) 1.420(2) -0.0175(16) 0.043(5) 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 O7 C1 117.27(9) . . ?
C20 O33 C34 115.63(11) . . ?
C2 N3 C16 121.94(10) . . ?
C2 N3 C4 123.06(10) . . ?
C16 N3 C4 113.12(9) . . ?
C8 C1 O7 115.26(11) . . ?
C8 C1 C2 121.07(12) . . ?
O7 C1 C2 123.61(11) . . ?
N3 C2 C11 120.72(11) . . ?
N3 C2 C1 122.54(11) . . ?
C11 C2 C1 116.73(11) . . ?
N3 C4 C18 103.00(9) . . ?
N3 C4 C5 109.62(9) . . ?
C18 C4 C5 116.22(10) . . ?
N3 C4 H4 108.1(9) . . ?
C18 C4 H4 110.7(9) . . ?
C5 C4 H4 108.8(9) . . ?
C12 C5 C6 118.38(11) . . ?
C12 C5 C4 125.96(11) . . ?
C6 C5 C4 115.57(11) . . ?
C15 C6 C5 121.88(12) . . ?
C15 C6 O7 119.33(11) . . ?
C5 C6 O7 118.68(11) . . ?
C1 C8 C9 121.27(13) . . ?
C1 C8 H8 116.6(11) . . ?
C9 C8 H8 122.1(11) . . ?
C8 C9 C10 118.72(12) . . ?
C8 C9 H9 123.4(11) . . ?
C10 C9 H9 117.9(11) . . ?
C9 C10 C11 120.42(13) . . ?
C9 C10 H10 118.5(10) . . ?
C11 C10 H10 121.0(10) . . ?
C10 C11 C2 121.78(12) . . ?
C10 C11 H11 118.3(9) . . ?
C2 C11 H11 119.9(9) . . ?
C5 C12 C13 120.43(12) . . ?
C5 C12 H12 118.9(10) . . ?
C13 C12 H12 120.6(10) . . ?
C14 C13 C12 120.01(13) . . ?
C14 C13 H13 119.8(10) . . ?
C12 C13 H13 120.1(10) . . ?
C13 C14 C15 120.33(12) . . ?
C13 C14 H14 120.4(12) . . ?
C15 C14 H14 119.3(12) . . ?
C6 C15 C14 118.97(13) . . ?
C6 C15 H15 119.7(11) . . ?
C14 C15 H15 121.3(11) . . ?
N3 C16 C17 101.52(9) . . ?
N3 C16 C19 113.66(10) . . ?
C17 C16 C19 113.71(10) . . ?
N3 C16 H16 113.7(9) . . ?
C17 C16 H16 107.2(9) . . ?
C19 C16 H16 107.0(9) . . ?
C18 C17 C20 129.66(11) . . ?
C18 C17 C16 112.72(10) . . ?
C20 C17 C16 117.46(10) . . ?
C17 C18 C21 130.00(11) . . ?
C17 C18 C4 109.60(10) . . ?
C21 C18 C4 119.96(10) . . ?
C22 C19 C26 119.40(12) . . ?
C22 C19 C16 120.41(11) . . ?
C26 C19 C16 120.18(11) . . ?
O32 C20 O33 123.71(11) . . ?
O32 C20 C17 125.93(11) . . ?
O33 C20 C17 110.32(10) . . ?
C31 C21 C27 117.56(11) . . ?
C31 C21 C18 119.37(10) . . ?
C27 C21 C18 123.03(11) . . ?
C19 C22 C23 120.38(12) . . ?
C19 C22 H22 118.3(10) . . ?
C23 C22 H22 121.3(10) . . ?
C24 C23 C22 119.93(13) . . ?
C24 C23 H23 118.9(11) . . ?
C22 C23 H23 121.1(11) . . ?
C23 C24 C25 120.14(13) . . ?
C23 C24 H24 120.3(11) . . ?
C25 C24 H24 119.6(11) . . ?
C24 C25 C26 120.13(13) . . ?
C24 C25 H25 120.2(11) . . ?
C26 C25 H25 119.6(11) . . ?
C19 C26 C25 120.00(13) . . ?
C19 C26 H26 117.3(11) . . ?
C25 C26 H26 122.7(11) . . ?
C28 C27 C21 121.04(12) . . ?
C28 C27 H27 119.5(11) . . ?
C21 C27 H27 119.5(11) . . ?
C27 C28 C29 120.59(12) . . ?
C27 C28 H28 119.5(11) . . ?
C29 C28 H28 119.9(11) . . ?
C30 C29 C28 119.13(12) . . ?
C30 C29 H29 118.6(10) . . ?
C28 C29 H29 122.2(10) . . ?
C29 C30 C31 120.49(12) . . ?
C29 C30 H30 120.0(9) . . ?
C31 C30 H30 119.5(9) . . ?
C30 C31 C21 121.15(11) . . ?
C30 C31 H31 118.4(10) . . ?
C21 C31 H31 120.4(10) . . ?
O33 C34 H341 110.9(11) . . ?
O33 C34 H342 110.4(13) . . ?
H341 C34 H342 112.4(17) . . ?
O33 C34 H343 104.4(12) . . ?
H341 C34 H343 110.1(15) . . ?
H342 C34 H343 108.4(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
O7 C6 1.3940(16) . ?
O7 C1 1.3981(15) . ?
O32 C20 1.2006(15) . ?
O33 C20 1.3378(15) . ?
O33 C34 1.4520(16) . ?
N3 C2 1.3870(15) . ?
N3 C16 1.4531(14) . ?
N3 C4 1.4657(15) . ?
C1 C8 1.3849(17) . ?
C1 C2 1.4133(17) . ?
C2 C11 1.4039(17) . ?
C4 C18 1.5135(16) . ?
C4 C5 1.5149(16) . ?
C4 H4 0.989(16) . ?
C5 C12 1.3917(17) . ?
C5 C6 1.3932(17) . ?
C6 C15 1.3871(17) . ?
C8 C9 1.387(2) . ?
C8 H8 0.987(18) . ?
C9 C10 1.389(2) . ?
C9 H9 0.996(19) . ?
C10 C11 1.3917(18) . ?
C10 H10 0.964(17) . ?
C11 H11 0.993(16) . ?
C12 C13 1.3967(18) . ?
C12 H12 0.972(16) . ?
C13 C14 1.388(2) . ?
C13 H13 0.963(18) . ?
C14 C15 1.389(2) . ?
C14 H14 0.955(19) . ?
C15 H15 0.964(19) . ?
C16 C17 1.5153(16) . ?
C16 C19 1.5261(16) . ?
C16 H16 0.995(16) . ?
C17 C18 1.3423(16) . ?
C17 C20 1.4917(16) . ?
C18 C21 1.4743(16) . ?
C19 C22 1.3888(17) . ?
C19 C26 1.3908(17) . ?
C21 C31 1.4031(16) . ?
C21 C27 1.4036(17) . ?
C22 C23 1.3931(18) . ?
C22 H22 0.976(18) . ?
C23 C24 1.378(2) . ?
C23 H23 1.01(2) . ?
C24 C25 1.385(2) . ?
C24 H24 1.012(19) . ?
C25 C26 1.392(2) . ?
C25 H25 1.00(2) . ?
C26 H26 1.017(19) . ?
C27 C28 1.3855(18) . ?
C27 H27 0.947(18) . ?
C28 C29 1.3910(19) . ?
C28 H28 0.985(19) . ?
C29 C30 1.3863(19) . ?
C29 H29 0.978(18) . ?
C30 C31 1.3881(17) . ?
C30 H30 0.983(16) . ?
C31 H31 0.986(17) . ?
C34 H341 1.004(19) . ?
C34 H342 0.94(2) . ?
C34 H343 0.97(2) . ?
