#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/22/2012266.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_2012266
loop_
_publ_author_name
'Bruno, Giuseppe'
'Nicoló, Francesco'
'Rotondo, Archimede'
'Gitto, Rosaria'
'Zappalá, Maria'
_publ_section_title
;
 4,5-Dihydro-7,8-dimethoxy-1-phenyl-3H-2,3-benzodiazepin-4-one
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1225
_journal_page_last               1227
_journal_paper_doi               10.1107/S0108270101011805
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C17 H16 N2 O3'
_chemical_formula_sum            'C17 H16 N2 O3'
_chemical_formula_weight         296.32
_chemical_name_common            'Ortho dimethoxybenzo-phenyldiazotropone'
_chemical_name_systematic
;
4,5-Dihydro-7,8-dimethoxy-1-phenyl-3H-2,3-benzodiazepin-4-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 95.600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.207(2)
_cell_length_b                   10.312(2)
_cell_length_c                   17.236(2)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      13.8
_cell_measurement_theta_min      6.43
_cell_volume                     1451.7(5)
_computing_cell_refinement       P3/V
_computing_data_collection       'P3/V (Siemens, 1989)'
_computing_data_reduction        'SHELXTL-Plus (Sheldrick, 1990)'
_computing_molecular_graphics    'XPW (Siemens, 1996)'
_computing_publication_material  'PARST97 (Nardelli, 1995) and SHELXL97'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .008
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2903
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.1
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 197
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             624
_exptl_crystal_size_max          .26
_exptl_crystal_size_mid          .24
_exptl_crystal_size_min          .12
_refine_diff_density_max         .16
_refine_diff_density_min         -.15
_refine_ls_extinction_coef       .0045(9)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   .839
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .839
_refine_ls_R_factor_all          .051
_refine_ls_R_factor_gt           .032
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0519P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .080
_reflns_number_gt                1734
_reflns_number_total             2567
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1067.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2012266
_cod_database_fobs_code          2012266
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 .44184(17) .62315(14) .58707(9) .0392(4) Uani d . 1 . . C
O1 .56570(12) .64626(10) .55456(7) .0502(3) Uani d . 1 . . O
N2 .33046(15) .53575(13) .55707(9) .0431(4) Uani d . 1 . . N
H2 .360(2) .4848(18) .5208(11) .066(6) Uiso d . 1 . . H
N3 .19281(14) .48951(12) .58928(8) .0418(3) Uani d . 1 . . N
C4 .09083(17) .56974(14) .61556(9) .0349(4) Uani d . 1 . . C
C5 .10517(16) .71263(13) .61856(8) .0324(3) Uani d . 1 . . C
C6 .25402(16) .77126(14) .64210(8) .0329(3) Uani d . 1 . . C
C7 .40348(16) .68860(15) .66093(9) .0398(4) Uani d . 1 . . C
H7A .4951 .7419 .6814 .048 Uiso calc R 1 . . H
H7B .383 .6243 .6999 .048 Uiso calc R 1 . . H
C8 .26573(16) .90642(14) .64534(8) .0360(4) Uani d . 1 . . C
H8 .3653 .9453 .662 .043 Uiso calc R 1 . . H
C9 .13049(17) .98247(13) .62402(8) .0344(4) Uani d . 1 . . C
C10 -.01944(15) .92377(14) .59857(8) .0318(3) Uani d . 1 . . C
C11 -.03263(16) .79086(14) .59738(8) .0332(3) Uani d . 1 . . C
H11 -.1333 .7523 .5825 .04 Uiso calc R 1 . . H
C12 -.05541(16) .50662(13) .64471(9) .0361(4) Uani d . 1 . . C
C13 -.11398(19) .38906(15) .61385(10) .0489(4) Uani d . 1 . . C
H13 -.0617 .3488 .5748 .059 Uiso calc R 1 . . H
C14 -.2495(2) .33216(17) .64108(12) .0632(5) Uani d . 1 . . C
H14 -.2881 .2537 .62 .076 Uiso calc R 1 . . H
C15 -.3284(2) .38962(17) .69880(11) .0574(5) Uani d . 1 . . C
H15 -.4208 .3511 .7161 .069 Uiso calc R 1 . . H
C16 -.26981(19) .50438(16) .73070(10) .0478(4) Uani d . 1 . . C
H16 -.3209 .543 .7707 .057 Uiso calc R 1 . . H
C17 -.13526(17) .56232(15) .70350(9) .0401(4) Uani d . 1 . . C
H17 -.0972 .6406 .7251 .048 Uiso calc R 1 . . H
O2 .12966(12) 1.11411(10) .62487(7) .0481(3) Uani d . 1 . . O
C18 .27701(19) 1.17974(16) .65132(10) .0524(4) Uani d . 1 . . C
H18A .259 1.2717 .6488 .079 Uiso calc R 1 . . H
H18B .3611 1.1569 .6188 .079 Uiso calc R 1 . . H
H18C .3105 1.155 .7042 .079 Uiso calc R 1 . . H
O3 -.14385(11) 1.00856(9) .57731(6) .0418(3) Uani d . 1 . . O
C19 -.30176(18) .95579(17) .55732(11) .0521(5) Uani d . 1 . . C
H19A -.3779 1.0247 .5436 .078 Uiso calc R 1 . . H
H19B -.336 .9088 .601 .078 Uiso calc R 1 . . H
H19C -.2985 .8981 .5138 .078 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .006 '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_publ_flag
O1 C1 N2 120.90(10) yes
O1 C1 C7 123.40(10) yes
N2 C1 C7 115.80(10) ?
C1 N2 N3 128.50(10) yes
C1 N2 H2 117.0(10) no
N3 N2 H2 112.0(10) no
N2 N3 C4 120.00(10) yes
N3 C4 C5 126.80(10) yes
N3 C4 C12 114.10(10) ?
C5 C4 C12 119.10(10) ?
C6 C5 C11 119.22(13) ?
C4 C5 C6 120.60(10) yes
C11 C5 C4 120.18(13) ?
C5 C6 C8 120.08(13) ?
C5 C6 C7 119.50(10) yes
C8 C6 C7 120.36(13) ?
C1 C7 C6 107.80(10) ?
C1 C7 H7A 110.1 ?
C6 C7 H7A 110.1 ?
C1 C7 H7B 110.1 ?
C6 C7 H7B 110.1 ?
H7A C7 H7B 108.5 ?
C9 C8 C6 120.39(13) ?
C9 C8 H8 119.8 ?
C6 C8 H8 119.8 ?
O2 C9 C8 124.78(13) ?
O2 C9 C10 115.45(12) ?
C8 C9 C10 119.77(13) ?
O3 C10 C11 125.31(12) ?
O3 C10 C9 114.67(12) ?
C11 C10 C9 120.01(13) ?
C10 C11 C5 120.48(13) ?
C10 C11 H11 119.8 ?
C5 C11 H11 119.8 ?
C17 C12 C13 118.11(14) ?
C17 C12 C4 121.23(13) ?
C13 C12 C4 120.66(14) ?
C14 C13 C12 120.04(16) ?
C14 C13 H13 120 ?
C12 C13 H13 120 ?
C15 C14 C13 121.04(17) ?
C15 C14 H14 119.5 ?
C13 C14 H14 119.5 ?
C16 C15 C14 119.39(16) ?
C16 C15 H15 120.3 ?
C14 C15 H15 120.3 ?
C15 C16 C17 119.95(16) ?
C15 C16 H16 120 ?
C17 C16 H16 120 ?
C16 C17 C12 121.45(15) ?
C16 C17 H17 119.3 ?
C12 C17 H17 119.3 ?
C9 O2 C18 118.30(10) yes
O2 C18 H18A 109.5 ?
O2 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
O2 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C10 O3 C19 117.50(10) yes
O3 C19 H19A 109.5 ?
O3 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
O3 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.231(2) yes
C1 N2 . 1.350(2) yes
C1 C7 . 1.501(2) yes
N2 N3 . 1.391(2) yes
N3 C4 . 1.290(2) yes
C4 C5 . 1.479(2) yes
C4 C12 . 1.495(2) no
C5 C6 . 1.388(2) yes
C5 C11 . 1.4080(19) ?
C6 C8 . 1.398(2) ?
C6 C7 . 1.503(2) yes
C8 C9 . 1.3793(19) ?
O2 C9 . 1.358(2) yes
O3 C10 . 1.367(2) yes
O2 C18 . 1.421(2) yes
O3 C19 . 1.417(2) yes
C9 C10 . 1.4027(19) ?
C10 C11 . 1.375(2) ?
C12 C17 . 1.384(2) ?
C12 C13 . 1.391(2) ?
C13 C14 . 1.380(2) ?
C14 C15 . 1.373(2) ?
C15 C16 . 1.372(2) ?
C16 C17 . 1.377(2) ?
N2 H2 . .87(2) ?
C7 H7A . .97 ?
C7 H7B . .97 ?
C8 H8 . .93 ?
C11 H11 . .93 ?
C13 H13 . .93 ?
C14 H14 . .93 ?
C15 H15 . .93 ?
C16 H16 . .93 ?
C17 H17 . .93 ?
C18 H18A . .96 ?
C18 H18B . .96 ?
C18 H18C . .96 ?
C19 H19A . .96 ?
C19 H19B . .96 ?
C19 H19C . .96 ?
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
N2 H2 O1 3_666 .87(2) 2.01(2) 2.876(2) 174(2)
C18 H18A N3 1_565 .96 2.51 3.418(2) 158
C13 H13 N3 . .93 2.54 2.793(2) 96
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
_geom_torsion_publ_flag
O1 C1 N2 N3 173.64(14) ?
C7 C1 N2 N3 -6.6(2) ?
C1 N2 N3 C4 50.0(2) ?
N2 N3 C4 C5 -2.5(2) ?
N2 N3 C4 C12 177.05(13) ?
N3 C4 C5 C6 -42.8(2) ?
C12 C4 C5 C6 137.75(14) ?
N3 C4 C5 C11 137.15(16) ?
C12 C4 C5 C11 -42.3(2) ?
C11 C5 C6 C8 .6(2) ?
C4 C5 C6 C8 -179.45(14) ?
C11 C5 C6 C7 -176.94(12) ?
C4 C5 C6 C7 3.0(2) ?
O1 C1 C7 C6 113.45(16) ?
N2 C1 C7 C6 -66.28(17) yes
C5 C6 C7 C1 65.53(17) ?
C8 C6 C7 C1 -112.03(15) ?
C5 C6 C8 C9 -1.1(2) ?
C7 C6 C8 C9 176.48(13) ?
C6 C8 C9 O2 -179.73(14) ?
C6 C8 C9 C10 -.3(2) ?
O2 C9 C10 O3 .88(19) ?
C8 C9 C10 O3 -178.59(12) ?
O2 C9 C10 C11 -178.38(13) ?
C8 C9 C10 C11 2.2(2) ?
O3 C10 C11 C5 178.23(13) ?
C9 C10 C11 C5 -2.6(2) ?
C6 C5 C11 C10 1.2(2) ?
C4 C5 C11 C10 -178.71(13) ?
N3 C4 C12 C17 150.78(14) ?
C5 C4 C12 C17 -29.7(2) yes
N3 C4 C12 C13 -28.5(2) ?
C5 C4 C12 C13 151.02(15) ?
C17 C12 C13 C14 1.0(2) ?
C4 C12 C13 C14 -179.72(15) ?
C12 C13 C14 C15 -.2(3) ?
C13 C14 C15 C16 -1.1(3) ?
C14 C15 C16 C17 1.5(3) ?
C15 C16 C17 C12 -.7(2) ?
C13 C12 C17 C16 -.5(2) ?
C4 C12 C17 C16 -179.83(13) ?
C8 C9 O2 C18 -1.6(2) yes
C10 C9 O2 C18 178.95(13) ?
C11 C10 O3 C19 4.4(2) yes
C9 C10 O3 C19 -174.81(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8036671
