#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/90/2019076.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_2019076
loop_
_publ_author_name
'Grinev, Vyacheslav S.'
'Egorova, Alevtina Yu.'
_publ_section_title
;
 3a-Phenyl-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-1-one,
 a potential plant-growth regulator
;
_journal_coeditor_code           EG3127
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              880
_journal_page_last               883
_journal_paper_doi               10.1107/S0108270113016119
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C16 H14 N2 O'
_chemical_formula_moiety         'C16 H14 N2 O'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29
_chemical_name_systematic
;
3a-Phenyl-2,3,3a,4-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]\
imidazol-1-one
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                66.8030(10)
_cell_angle_beta                 88.947(2)
_cell_angle_gamma                82.509(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2966(9)
_cell_length_b                   9.1081(11)
_cell_length_c                   10.3723(12)
_cell_measurement_reflns_used    354
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29
_cell_measurement_theta_min      3
_cell_volume                     627.78(13)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7155
_diffrn_reflns_theta_full        29.57
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.409
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0456
_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)+(0.0792P)²+0.2300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                3259
_reflns_number_total             3492
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            eg3127.cif
_cod_data_source_block           I
_cod_database_code               2019076
_cod_database_fobs_code          2019076
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
N N1 0.61829(11) 0.02564(9) 0.61171(8) 0.01383(17) Uani d . 1 1
H H1N 0.493(2) 0.0435(19) 0.6207(17) 0.030(4) Uiso d . 1 1
N N2 0.90402(10) 0.01688(9) 0.70692(8) 0.01328(16) Uani d . 1 1
O O1 1.21712(9) 0.01286(9) 0.67719(8) 0.01995(17) Uani d . 1 1
C C1 1.06087(12) 0.08609(11) 0.65663(9) 0.01507(18) Uani d . 1 1
C C2 0.99897(13) 0.26406(11) 0.57228(10) 0.01707(19) Uani d . 1 1
H H2A 1.0777 0.3076 0.4907 0.020 Uiso calc R 1 1
H H2B 1.0020 0.3270 0.6311 0.020 Uiso calc R 1 1
C C3 0.79979(12) 0.26642(11) 0.52490(10) 0.01545(18) Uani d . 1 1
H H3A 0.7976 0.2467 0.4377 0.019 Uiso calc R 1 1
H H3B 0.7237 0.3707 0.5092 0.019 Uiso calc R 1 1
C C4 0.73073(12) 0.12709(10) 0.64971(9) 0.01247(17) Uani d . 1 1
C C5 0.69624(12) -0.13486(10) 0.68207(9) 0.01322(18) Uani d . 1 1
C C6 0.62667(13) -0.27503(11) 0.69730(10) 0.01614(19) Uani d . 1 1
H H6A 0.5072 -0.2713 0.6603 0.019 Uiso calc R 1 1
C C7 0.73790(13) -0.42250(11) 0.76887(10) 0.01738(19) Uani d . 1 1
H H7A 0.6929 -0.5199 0.7800 0.021 Uiso calc R 1 1
C C8 0.91289(13) -0.42918(11) 0.82398(10) 0.01699(19) Uani d . 1 1
H H8A 0.9852 -0.5308 0.8720 0.020 Uiso calc R 1 1
C C9 0.98365(12) -0.28751(11) 0.80946(10) 0.01587(19) Uani d . 1 1
H H9A 1.1027 -0.2908 0.8468 0.019 Uiso calc R 1 1
C C10 0.87283(12) -0.14334(10) 0.73858(9) 0.01316(18) Uani d . 1 1
C C11 0.63184(12) 0.18362(10) 0.75601(9) 0.01345(18) Uani d . 1 1
C C12 0.46662(13) 0.28868(12) 0.71129(10) 0.01736(19) Uani d . 1 1
H H12A 0.4231 0.3254 0.6166 0.021 Uiso calc R 1 1
C C13 0.36550(14) 0.33989(13) 0.80441(11) 0.0213(2) Uani d . 1 1
H H13A 0.2537 0.4118 0.7730 0.026 Uiso calc R 1 1
C C14 0.42789(15) 0.28592(13) 0.94374(11) 0.0215(2) Uani d . 1 1
H H14A 0.3586 0.3206 1.0074 0.026 Uiso calc R 1 1
C C15 0.59126(15) 0.18152(12) 0.98899(10) 0.0204(2) Uani d . 1 1
H H15A 0.6339 0.1445 1.0839 0.025 Uiso calc R 1 1
C C16 0.69403(13) 0.13019(11) 0.89523(10) 0.01684(19) Uani d . 1 1
H H16A 0.8062 0.0589 0.9267 0.020 Uiso calc R 1 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'
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
C5 N1 C4 107.81(7)
C5 N1 H1N 114.1(10)
C4 N1 H1N 116.3(10)
C1 N2 C10 128.12(8)
C1 N2 C4 113.60(7)
C10 N2 C4 109.45(7)
O1 C1 N2 124.57(9)
O1 C1 C2 128.65(8)
N2 C1 C2 106.78(7)
C1 C2 C3 102.85(7)
C1 C2 H2A 111.2
C3 C2 H2A 111.2
C1 C2 H2B 111.2
C3 C2 H2B 111.2
H2A C2 H2B 109.1
C2 C3 C4 103.00(7)
C2 C3 H3A 111.2
C4 C3 H3A 111.2
C2 C3 H3B 111.2
C4 C3 H3B 111.2
H3A C3 H3B 109.1
N1 C4 N2 102.36(7)
N1 C4 C11 110.26(7)
N2 C4 C11 113.36(7)
N1 C4 C3 115.50(7)
N2 C4 C3 102.07(7)
C11 C4 C3 112.65(7)
C6 C5 N1 129.53(8)
C6 C5 C10 119.99(8)
N1 C5 C10 110.45(8)
C5 C6 C7 118.01(8)
C5 C6 H6A 121.0
C7 C6 H6A 121.0
C8 C7 C6 121.42(9)
C8 C7 H7A 119.3
C6 C7 H7A 119.3
C7 C8 C9 120.80(8)
C7 C8 H8A 119.6
C9 C8 H8A 119.6
C10 C9 C8 117.14(8)
C10 C9 H9A 121.4
C8 C9 H9A 121.4
C9 C10 C5 122.64(8)
C9 C10 N2 130.60(8)
C5 C10 N2 106.76(7)
C16 C11 C12 119.26(8)
C16 C11 C4 123.18(8)
C12 C11 C4 117.49(8)
C13 C12 C11 120.48(9)
C13 C12 H12A 119.8
C11 C12 H12A 119.8
C12 C13 C14 120.11(9)
C12 C13 H13A 119.9
C14 C13 H13A 119.9
C15 C14 C13 119.78(9)
C15 C14 H14A 120.1
C13 C14 H14A 120.1
C14 C15 C16 120.27(9)
C14 C15 H15A 119.9
C16 C15 H15A 119.9
C11 C16 C15 120.09(9)
C11 C16 H16A 120.0
C15 C16 H16A 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.3968(11)
N1 C4 1.4761(11)
N1 H1N 0.914(16)
N2 C1 1.3735(11)
N2 C10 1.4126(11)
N2 C4 1.4785(11)
O1 C1 1.2201(11)
C1 C2 1.5177(13)
C2 C3 1.5375(13)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.5456(12)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C11 1.5240(12)
C5 C6 1.3855(12)
C5 C10 1.4057(12)
C6 C7 1.4022(13)
C6 H6A 0.9500
C7 C8 1.3928(13)
C7 H7A 0.9500
C8 C9 1.4043(13)
C8 H8A 0.9500
C9 C10 1.3795(12)
C9 H9A 0.9500
C11 C16 1.3932(13)
C11 C12 1.3979(12)
C12 C13 1.3907(13)
C12 H12A 0.9500
C13 C14 1.3941(15)
C13 H13A 0.9500
C14 C15 1.3853(15)
C14 H14A 0.9500
C15 C16 1.4023(13)
C15 H15A 0.9500
C16 H16A 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N O1 1_455 0.914(16) 2.112(17) 2.9994(11) 163.4(14)
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
C10 N2 C1 O1 -27.81(15)
C4 N2 C1 O1 -171.39(9)
C10 N2 C1 C2 151.31(9)
C4 N2 C1 C2 7.74(10)
O1 C1 C2 C3 152.84(9)
N2 C1 C2 C3 -26.24(9)
C1 C2 C3 C4 33.88(9)
C5 N1 C4 N2 17.45(9)
C5 N1 C4 C11 -103.45(8)
C5 N1 C4 C3 127.43(8)
C1 N2 C4 N1 133.80(8)
C10 N2 C4 N1 -16.51(9)
C1 N2 C4 C11 -107.46(8)
C10 N2 C4 C11 102.23(8)
C1 N2 C4 C3 13.96(9)
C10 N2 C4 C3 -136.34(7)
C2 C3 C4 N1 -139.28(8)
C2 C3 C4 N2 -29.13(8)
C2 C3 C4 C11 92.78(8)
C4 N1 C5 C6 169.27(9)
C4 N1 C5 C10 -12.80(10)
N1 C5 C6 C7 177.26(9)
C10 C5 C6 C7 -0.50(13)
C5 C6 C7 C8 0.30(14)
C6 C7 C8 C9 0.02(14)
C7 C8 C9 C10 -0.13(14)
C8 C9 C10 C5 -0.07(14)
C8 C9 C10 N2 -179.87(9)
C6 C5 C10 C9 0.40(14)
N1 C5 C10 C9 -177.76(8)
C6 C5 C10 N2 -179.76(8)
N1 C5 C10 N2 2.08(10)
C1 N2 C10 C9 44.60(15)
C4 N2 C10 C9 -170.65(9)
C1 N2 C10 C5 -135.22(9)
C4 N2 C10 C5 9.53(9)
N1 C4 C11 C16 111.04(9)
N2 C4 C11 C16 -3.03(12)
C3 C4 C11 C16 -118.31(9)
N1 C4 C11 C12 -66.08(10)
N2 C4 C11 C12 179.85(8)
C3 C4 C11 C12 64.57(10)
C16 C11 C12 C13 0.20(14)
C4 C11 C12 C13 177.44(8)
C11 C12 C13 C14 -0.35(15)
C12 C13 C14 C15 0.21(16)
C13 C14 C15 C16 0.08(15)
C12 C11 C16 C15 0.09(14)
C4 C11 C16 C15 -176.98(8)
C14 C15 C16 C11 -0.23(15)
