#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/53/2205383.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_2205383
loop_
_publ_author_name
'Xiang-Chao Zeng'
'Shi-Hai Xu'
'Jian Gu'
'Dong-Sheng Deng'
_publ_section_title
1-Methyl-6,7-dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o795
_journal_page_last               o796
_journal_paper_doi               10.1107/S1600536805005532
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C9 H10 N2 O2'
_chemical_formula_moiety         'C9 H10 N2 O2'
_chemical_formula_sum            'C9 H10 N2 O2'
_chemical_formula_weight         178.19
_chemical_melting_point          471
_chemical_name_systematic
;
1-Methyl-6,7-dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.589(3)
_cell_length_b                   8.686(3)
_cell_length_c                   11.375(4)
_cell_measurement_reflns_used    863
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.87
_cell_measurement_theta_min      2.97
_cell_volume                     848.6(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker,1999)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker,1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5343
_diffrn_reflns_theta_full        27.05
_diffrn_reflns_theta_max         27.05
_diffrn_reflns_theta_min         2.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick,1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0316
_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)+(0.0557P)²+0.1067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                991
_reflns_number_total             1088
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6329.cif
_cod_data_source_block           I
_cod_depositor_comments
;
 Moving the _geom_hbond_site_symmetry_A, _geom_hbond_distance_DH,
 _geom_hbond_distance_HA, _geom_hbond_distance_DA, _geom_hbond_angle_DHA,
 _geom_hbond_publ_flag data items into the main _geom_hbond loop.

 Antanas Vaitkus,
 2017-01-29

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2205383
_cod_database_fobs_code          2205383
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_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_type_symbol
O1 0.04462(17) 0.86100(16) 0.20396(14) 0.0553(4) Uani d . 1 O
O2 0.4332(2) 0.41611(16) 0.40611(13) 0.0603(4) Uani d . 1 O
C1 0.3491(3) 0.8785(2) 0.48757(17) 0.0486(5) Uani d . 1 C
H1 0.3693 0.9474 0.5482 0.058 Uiso calc R 1 H
C2 0.3976(2) 0.7293(2) 0.48375(17) 0.0463(5) Uani d . 1 C
H2 0.4548 0.6780 0.5411 0.056 Uiso calc R 1 H
C3 0.3444(2) 0.6670(2) 0.37587(16) 0.0377(4) Uani d . 1 C
C4 0.2610(2) 0.78326(19) 0.31886(15) 0.0360(4) Uani d . 1 C
C5 0.1620(2) 0.78013(19) 0.21187(16) 0.0381(4) Uani d . 1 C
C6 0.3399(2) 0.5856(2) 0.12434(16) 0.0421(4) Uani d . 1 C
H6A 0.4318 0.6481 0.1375 0.051 Uiso calc R 1 H
H6B 0.3491 0.5396 0.0469 0.051 Uiso calc R 1 H
C7 0.3353(3) 0.4587(2) 0.21540(18) 0.0442(4) Uani d . 1 C
H7A 0.2319 0.4138 0.2155 0.053 Uiso calc R 1 H
H7B 0.4079 0.3788 0.1922 0.053 Uiso calc R 1 H
C8 0.3740(2) 0.5086(2) 0.33844(16) 0.0396(4) Uani d . 1 C
C9 0.2061(3) 1.0644(2) 0.3625(2) 0.0588(6) Uani d . 1 C
H9A 0.2253 1.1314 0.4280 0.088 Uiso calc R 1 H
H9B 0.0961 1.0582 0.3482 0.088 Uiso calc R 1 H
H9C 0.2572 1.1043 0.2939 0.088 Uiso calc R 1 H
N1 0.26655(19) 0.91067(17) 0.38880(14) 0.0415(4) Uani d . 1 N
N2 0.20374(18) 0.68391(18) 0.12651(14) 0.0427(4) Uani d . 1 N
H2A 0.1435 0.6796 0.0662 0.051 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0505(8) 0.0500(8) 0.0654(9) 0.0118(7) -0.0083(7) -0.0023(7)
O2 0.0819(11) 0.0502(8) 0.0490(8) 0.0186(8) 0.0033(8) 0.0124(7)
C1 0.0553(11) 0.0513(10) 0.0394(9) -0.0077(10) 0.0038(9) -0.0100(9)
C2 0.0528(11) 0.0521(11) 0.0341(9) -0.0020(9) -0.0011(8) 0.0020(8)
C3 0.0400(8) 0.0388(8) 0.0343(8) -0.0020(8) 0.0036(7) 0.0030(7)
C4 0.0371(8) 0.0327(8) 0.0382(9) -0.0030(7) 0.0060(7) -0.0001(7)
C5 0.0379(8) 0.0341(8) 0.0424(9) -0.0019(8) 0.0006(7) 0.0053(7)
C6 0.0449(9) 0.0466(9) 0.0350(8) 0.0019(9) 0.0050(8) -0.0042(8)
C7 0.0487(10) 0.0370(8) 0.0470(10) 0.0027(8) 0.0041(9) -0.0040(8)
C8 0.0419(10) 0.0377(8) 0.0393(9) 0.0026(8) 0.0072(7) 0.0071(8)
C9 0.0639(13) 0.0349(9) 0.0776(16) 0.0030(9) 0.0029(12) -0.0073(10)
N1 0.0448(8) 0.0360(7) 0.0436(8) -0.0006(7) 0.0061(7) -0.0058(7)
N2 0.0455(8) 0.0468(8) 0.0357(8) 0.0018(7) -0.0047(6) -0.0003(7)
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
N1 C1 C2 109.23(17)
N1 C1 H1 125.4
C2 C1 H1 125.4
C1 C2 C3 107.00(18)
C1 C2 H2 126.5
C3 C2 H2 126.5
C4 C3 C2 106.92(16)
C4 C3 C8 129.35(17)
C2 C3 C8 123.73(17)
N1 C4 C3 107.34(16)
N1 C4 C5 120.86(15)
C3 C4 C5 131.33(16)
O1 C5 N2 121.70(18)
O1 C5 C4 121.20(17)
N2 C5 C4 117.09(15)
N2 C6 C7 113.37(15)
N2 C6 H6A 108.9
C7 C6 H6A 108.9
N2 C6 H6B 108.9
C7 C6 H6B 108.9
H6A C6 H6B 107.7
C8 C7 C6 114.97(15)
C8 C7 H7A 108.5
C6 C7 H7A 108.5
C8 C7 H7B 108.5
C6 C7 H7B 108.5
H7A C7 H7B 107.5
O2 C8 C3 120.47(17)
O2 C8 C7 119.26(17)
C3 C8 C7 120.25(16)
N1 C9 H9A 109.5
N1 C9 H9B 109.5
H9A C9 H9B 109.5
N1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C1 N1 C4 109.49(15)
C1 N1 C9 122.87(17)
C4 N1 C9 127.48(17)
C5 N2 C6 126.91(15)
C5 N2 H2A 116.5
C6 N2 H2A 116.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.232(2)
O2 C8 1.223(2)
C1 N1 1.358(3)
C1 C2 1.362(3)
C1 H1 0.9300
C2 C3 1.417(3)
C2 H2 0.9300
C3 C4 1.398(2)
C3 C8 1.462(2)
C4 N1 1.364(2)
C4 C5 1.485(3)
C5 N2 1.330(2)
C6 N2 1.448(2)
C6 C7 1.513(3)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.502(3)
C7 H7A 0.9700
C7 H7B 0.9700
C9 N1 1.463(2)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
N2 H2A 0.8600
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
_geom_hbond_publ_flag
N2 H2A O2 2_564 0.86 2.11 2.902(2) 153 y
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
N1 C1 C2 C3 1.1(2)
C1 C2 C3 C4 -1.3(2)
C1 C2 C3 C8 179.56(17)
C2 C3 C4 N1 1.0(2)
C8 C3 C4 N1 -179.88(17)
C2 C3 C4 C5 -170.87(18)
C8 C3 C4 C5 8.2(3)
N1 C4 C5 O1 -26.5(3)
C3 C4 C5 O1 144.5(2)
N1 C4 C5 N2 154.99(17)
C3 C4 C5 N2 -34.0(3)
N2 C6 C7 C8 -77.9(2)
C4 C3 C8 O2 -170.83(19)
C2 C3 C8 O2 8.1(3)
C4 C3 C8 C7 10.5(3)
C2 C3 C8 C7 -170.54(18)
C6 C7 C8 O2 -151.04(18)
C6 C7 C8 C3 27.6(3)
C2 C1 N1 C4 -0.4(2)
C2 C1 N1 C9 -176.17(19)
C3 C4 N1 C1 -0.4(2)
C5 C4 N1 C1 172.52(16)
C3 C4 N1 C9 175.10(18)
C5 C4 N1 C9 -12.0(3)
O1 C5 N2 C6 178.71(16)
C4 C5 N2 C6 -2.8(3)
C7 C6 N2 C5 66.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8662950
