#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151857.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_7151857
loop_
_publ_author_name
'Khlebnikov, Alexander F.'
'Novikov, Mikhail S.'
'Golovkina, Maria V.'
'Petrovskii, Petr P.'
'Konev, Alexander S.'
'Yufit, Dmitry S.'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 An efficient approach to azirino and pyrrolo-fused dibenzazepines.
 Conformations of substituted dibenzo[c,f]pyrrolo[1,2-a]azepines.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3886
_journal_page_last               3895
_journal_paper_doi               10.1039/c1ob05081h
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H19 N3'
_chemical_formula_sum            'C25 H19 N3'
_chemical_formula_weight         361.43
_chemical_melting_point          478.15
_chemical_name_systematic
;
(1RS,2RS,3SR,13bRS)-3-Phenyl-2,3,9,13b-tetrahydro-1H-
dibenzo[c,f]pyrrolo[1,2-a]azepine-1,2-dicarbonitrile
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.290(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.6196(2)
_cell_length_b                   5.85170(10)
_cell_length_c                   12.6336(2)
_cell_measurement_reflns_used    2594
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      57.631
_cell_measurement_theta_min      3.545
_cell_volume                     920.71(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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
;
A short history of SHELX (Sheldrick, 2007)/Bruker
;
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_source         'Microstar rotating anode'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54188
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3871
_diffrn_reflns_theta_full        55.92
_diffrn_reflns_theta_max         55.92
_diffrn_reflns_theta_min         3.54
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.0499 before and 0.0335 after correction.
The Ratio of minimum to maximum transmission is 0.871.
The λ/2 correction factor is Not present
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whitish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         2041
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0331
_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+0.0400P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                1946
_reflns_number_total             2041
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05081h.txt
_cod_data_source_block           18_DAX18
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '205 C' was changed to '478.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        920.71(3)
_cod_database_code               7151857
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.10387(16) 0.0784(4) 0.49534(17) 0.0293(5) Uani 1 1 d . . .
N2 N 0.02791(18) 0.9060(4) 0.72339(17) 0.0313(6) Uani 1 1 d . . .
N4 N 0.27495(14) 0.5760(3) 0.73444(15) 0.0189(5) Uani 1 1 d . . .
C1 C 0.14131(18) 0.4788(4) 0.5853(2) 0.0206(6) Uani 1 1 d . . .
C2 C 0.09507(18) 0.4906(4) 0.69168(19) 0.0200(6) Uani 1 1 d . . .
C3 C 0.19439(18) 0.4366(4) 0.77615(19) 0.0186(5) Uani 1 1 d . . .
C4A C 0.38283(18) 0.5835(4) 0.79101(18) 0.0187(6) Uani 1 1 d . . .
C5 C 0.42750(18) 0.4187(4) 0.86398(18) 0.0199(6) Uani 1 1 d . . .
C6 C 0.53159(18) 0.4422(5) 0.91690(19) 0.0225(6) Uani 1 1 d . . .
C7 C 0.59175(19) 0.6307(4) 0.89843(19) 0.0226(6) Uani 1 1 d . . .
C8 C 0.54707(19) 0.7967(4) 0.8268(2) 0.0208(6) Uani 1 1 d . . .
C8A C 0.44295(19) 0.7759(4) 0.77192(18) 0.0193(6) Uani 1 1 d . . .
C9 C 0.39203(19) 0.9531(4) 0.6941(2) 0.0217(6) Uani 1 1 d . . .
C9A C 0.36882(18) 0.8762(4) 0.57868(19) 0.0200(6) Uani 1 1 d . . .
C10 C 0.40486(19) 1.0124(5) 0.5005(2) 0.0243(6) Uani 1 1 d . . .
C11 C 0.3836(2) 0.9554(5) 0.3928(2) 0.0279(6) Uani 1 1 d . . .
C12 C 0.3284(2) 0.7585(5) 0.3609(2) 0.0271(6) Uani 1 1 d . . .
C13 C 0.29393(19) 0.6190(5) 0.4375(2) 0.0242(6) Uani 1 1 d . . .
C13A C 0.31213(18) 0.6776(4) 0.5459(2) 0.0201(6) Uani 1 1 d . . .
C13B C 0.26547(17) 0.5139(4) 0.61982(18) 0.0180(5) Uani 1 1 d . . .
C14 C 0.11925(18) 0.2566(5) 0.5336(2) 0.0221(6) Uani 1 1 d . . .
C15 C 0.05594(18) 0.7236(5) 0.70915(19) 0.0222(6) Uani 1 1 d . . .
C16 C 0.17860(17) 0.4818(4) 0.89029(19) 0.0194(6) Uani 1 1 d . . .
C17 C 0.12533(18) 0.3140(4) 0.9407(2) 0.0236(6) Uani 1 1 d . . .
C18 C 0.10418(19) 0.3483(4) 1.0438(2) 0.0250(6) Uani 1 1 d . . .
C19 C 0.13667(18) 0.5462(4) 1.0980(2) 0.0259(6) Uani 1 1 d . . .
C20 C 0.18923(18) 0.7145(5) 1.0485(2) 0.0265(6) Uani 1 1 d . . .
C21 C 0.20925(19) 0.6814(4) 0.9448(2) 0.0229(6) Uani 1 1 d . . .
H1 H 0.1118(17) 0.597(4) 0.5354(18) 0.014(6) Uiso 1 1 d . . .
H2 H 0.032(2) 0.384(5) 0.698(2) 0.036(7) Uiso 1 1 d . . .
H3 H 0.2089(18) 0.272(5) 0.7651(17) 0.017(6) Uiso 1 1 d . . .
H5 H 0.3862(18) 0.292(4) 0.8769(18) 0.014(6) Uiso 1 1 d . . .
H6 H 0.5605(16) 0.325(4) 0.9674(19) 0.009(6) Uiso 1 1 d . . .
H7 H 0.6632(18) 0.648(4) 0.9393(17) 0.017(6) Uiso 1 1 d . . .
H8 H 0.5880(18) 0.935(4) 0.8147(17) 0.012(5) Uiso 1 1 d . . .
H9A H 0.3257(18) 1.002(4) 0.7178(18) 0.010(5) Uiso 1 1 d . . .
H9B H 0.4364(18) 1.096(5) 0.6974(17) 0.018(6) Uiso 1 1 d . . .
H10 H 0.4460(19) 1.140(5) 0.5209(19) 0.023(7) Uiso 1 1 d . . .
H11 H 0.409(2) 1.059(5) 0.337(2) 0.037(7) Uiso 1 1 d . . .
H12 H 0.3109(19) 0.711(4) 0.283(2) 0.027(7) Uiso 1 1 d . . .
H13 H 0.260(2) 0.481(5) 0.4143(19) 0.023(7) Uiso 1 1 d . . .
H13A H 0.2987(16) 0.361(4) 0.6145(17) 0.010(6) Uiso 1 1 d . . .
H17 H 0.1034(19) 0.173(5) 0.9007(19) 0.026(7) Uiso 1 1 d . . .
H18 H 0.062(2) 0.227(5) 1.076(2) 0.037(7) Uiso 1 1 d . . .
H19 H 0.124(2) 0.571(5) 1.168(2) 0.030(7) Uiso 1 1 d . . .
H20 H 0.211(2) 0.860(5) 1.085(2) 0.028(7) Uiso 1 1 d . . .
H21 H 0.2431(18) 0.797(4) 0.9133(18) 0.015(6) 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 0.0181 0.0091 '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 0.0311 0.0180 '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
N1 C14 C1 178.0(3) . . ?
N2 C15 C2 178.5(3) . . ?
N4 C3 C2 99.82(18) . . ?
N4 C3 C16 116.87(19) . . ?
N4 C3 H3 109.6(13) . . ?
N4 C13B C1 102.92(17) . . ?
N4 C13B C13A 117.91(19) . . ?
N4 C13B H13A 108.6(13) . . ?
C1 C2 H2 116.3(15) . . ?
C1 C13B H13A 106.0(12) . . ?
C2 C1 C13B 104.55(17) . . ?
C2 C1 H1 111.9(14) . . ?
C2 C3 H3 104.4(13) . . ?
C3 N4 C13B 105.31(17) . . ?
C3 C2 C1 102.32(18) . . ?
C3 C2 H2 112.5(15) . . ?
C4A N4 C3 119.74(18) . . ?
C4A N4 C13B 114.59(18) . . ?
C4A C5 H5 119.2(13) . . ?
C4A C8A C9 118.8(2) . . ?
C5 C4A N4 124.1(2) . . ?
C5 C4A C8A 120.0(2) . . ?
C5 C6 H6 118.4(12) . . ?
C6 C5 C4A 120.3(2) . . ?
C6 C5 H5 120.5(13) . . ?
C6 C7 C8 119.6(2) . . ?
C6 C7 H7 119.0(13) . . ?
C7 C6 C5 120.2(2) . . ?
C7 C6 H6 121.4(12) . . ?
C7 C8 C8A 121.2(2) . . ?
C7 C8 H8 120.7(12) . . ?
C8 C7 H7 121.3(14) . . ?
C8 C8A C4A 118.7(2) . . ?
C8 C8A C9 122.5(2) . . ?
C8A C4A N4 115.88(19) . . ?
C8A C8 H8 118.1(12) . . ?
C8A C9 C9A 115.0(2) . . ?
C8A C9 H9A 107.5(13) . . ?
C8A C9 H9B 111.8(12) . . ?
C9A C9 H9A 110.0(13) . . ?
C9A C9 H9B 108.0(13) . . ?
C9A C10 H10 119.7(15) . . ?
C9A C13A C13 119.5(2) . . ?
C9A C13A C13B 125.0(2) . . ?
C10 C9A C9 118.5(2) . . ?
C10 C11 H11 120.4(15) . . ?
C11 C10 C9A 121.5(3) . . ?
C11 C10 H10 118.8(15) . . ?
C11 C12 C13 119.4(2) . . ?
C11 C12 H12 122.5(15) . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 119.6(15) . . ?
C12 C13 C13A 121.3(3) . . ?
C12 C13 H13 117.9(15) . . ?
C13 C12 H12 118.2(15) . . ?
C13 C13A C13B 115.4(2) . . ?
C13A C9A C9 123.2(2) . . ?
C13A C9A C10 118.3(2) . . ?
C13A C13 H13 120.8(15) . . ?
C13A C13B C1 112.28(19) . . ?
C13A C13B H13A 108.4(13) . . ?
C13B C1 H1 110.5(13) . . ?
C14 C1 C2 110.8(2) . . ?
C14 C1 C13B 110.5(2) . . ?
C14 C1 H1 108.5(13) . . ?
C15 C2 C1 110.61(19) . . ?
C15 C2 C3 109.83(19) . . ?
C15 C2 H2 105.4(15) . . ?
C16 C3 C2 114.03(18) . . ?
C16 C3 H3 111.0(13) . . ?
C16 C17 H17 118.1(15) . . ?
C16 C21 C20 120.7(2) . . ?
C16 C21 H21 121.0(15) . . ?
C17 C16 C3 117.3(2) . . ?
C17 C18 H18 118.4(17) . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 121.5(15) . . ?
C18 C19 C20 119.9(2) . . ?
C18 C19 H19 121.2(17) . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 121.3(16) . . ?
C19 C20 H20 121.2(15) . . ?
C20 C19 H19 118.9(17) . . ?
C20 C21 H21 118.3(15) . . ?
C21 C16 C3 123.7(2) . . ?
C21 C16 C17 118.9(2) . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 118.9(15) . . ?
H9A C9 H9B 104.0(18) . . ?
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
N1 C14 1.153(3) . ?
N2 C15 1.148(3) . ?
N4 C3 1.466(3) . ?
N4 C4A 1.432(3) . ?
N4 C13B 1.479(3) . ?
C1 C2 1.551(3) . ?
C1 C13B 1.571(3) . ?
C1 C14 1.461(4) . ?
C1 H1 0.97(2) . ?
C2 C3 1.542(3) . ?
C2 C15 1.479(4) . ?
C2 H2 1.03(3) . ?
C3 C16 1.510(3) . ?
C3 H3 1.00(3) . ?
C4A C5 1.389(3) . ?
C4A C8A 1.400(4) . ?
C5 C6 1.381(3) . ?
C5 H5 0.94(3) . ?
C6 C7 1.380(4) . ?
C6 H6 0.97(2) . ?
C7 C8 1.384(4) . ?
C7 H7 0.97(2) . ?
C8 C8A 1.389(3) . ?
C8 H8 0.99(2) . ?
C8A C9 1.501(3) . ?
C9 C9A 1.509(3) . ?
C9 H9A 0.98(2) . ?
C9 H9B 1.00(3) . ?
C9A C10 1.401(3) . ?
C9A C13A 1.392(3) . ?
C10 C11 1.385(4) . ?
C10 H10 0.92(3) . ?
C11 C12 1.372(4) . ?
C11 H11 1.02(3) . ?
C12 C13 1.389(4) . ?
C12 H12 1.02(3) . ?
C13 C13A 1.394(4) . ?
C13 H13 0.94(3) . ?
C13A C13B 1.522(3) . ?
C13B H13A 1.00(2) . ?
C16 C17 1.400(3) . ?
C16 C21 1.379(3) . ?
C17 C18 1.386(4) . ?
C17 H17 0.98(3) . ?
C18 C19 1.374(4) . ?
C18 H18 1.01(3) . ?
C19 C20 1.391(4) . ?
C19 H19 0.93(3) . ?
C20 C21 1.388(4) . ?
C20 H20 0.99(3) . ?
C21 H21 0.92(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190664
