#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:28:16 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180395 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/64/7206446.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_7206446
loop_
_publ_author_name
'Cheng, Chuang'
'Jiang, Bo'
'Tu, Shu-Jiang'
'Li, Guigen'
_publ_section_title
;
 [4+2+1] Domino cyclization in water for chemo- and regioselective
 synthesis of spiro-substituted benzo[b]furo[3,4-e][1,4]diazepine
 derivatives
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              2107
_journal_paper_doi               10.1039/c1gc15183e
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C15 H7 Cl N2 O'
_chemical_formula_weight         266.68
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 117.940(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4701(15)
_cell_length_b                   3.8350(5)
_cell_length_c                   25.500(2)
_cell_measurement_reflns_used    615
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.329
_cell_measurement_theta_min      3.019
_cell_volume                     1163.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0988
_diffrn_reflns_av_sigmaI/netI    0.1136
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5292
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.8699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.1814
_refine_ls_R_factor_gt           0.1056
_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)+(0.0996P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2202
_refine_ls_wR_factor_ref         0.2515
_reflns_number_gt                956
_reflns_number_total             2018
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1gc15183e.txt
_cod_data_source_block           101104a
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7206446
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Cl1 Cl 0.89070(15) 0.7072(6) 0.20050(9) 0.0716(8) Uani 1 1 d .
N1 N 0.4274(5) 0.2241(16) 0.0513(2) 0.0528(15) Uani 1 1 d .
N2 N 0.4881(4) 0.5640(15) 0.1636(2) 0.0444(14) Uani 1 1 d .
O1 O 0.1795(4) 0.0630(15) -0.0049(2) 0.0697(16) Uani 1 1 d .
C1 C 0.2335(6) 0.2116(18) 0.0431(3) 0.0478(17) Uani 1 1 d .
C2 C 0.3589(5) 0.2870(17) 0.0722(3) 0.0409(16) Uani 1 1 d .
C3 C 0.3865(5) 0.4612(17) 0.1274(3) 0.0442(17) Uani 1 1 d .
C4 C 0.2837(5) 0.4923(18) 0.1334(3) 0.0463(18) Uani 1 1 d .
C5 C 0.1936(6) 0.3473(18) 0.0838(3) 0.0497(18) Uani 1 1 d .
C6 C 0.0860(6) 0.347(2) 0.0792(3) 0.060(2) Uani 1 1 d .
H6 H 0.0248 0.2544 0.0462 0.072 Uiso 1 1 calc R
C7 C 0.0744(7) 0.493(3) 0.1262(4) 0.074(3) Uani 1 1 d .
H7 H 0.0037 0.4951 0.1243 0.089 Uiso 1 1 calc R
C8 C 0.1615(7) 0.629(2) 0.1741(4) 0.074(2) Uani 1 1 d .
H8 H 0.1504 0.7271 0.2043 0.089 Uiso 1 1 calc R
C9 C 0.2684(6) 0.6242(19) 0.1787(3) 0.054(2) Uani 1 1 d .
H9 H 0.3293 0.7106 0.2126 0.065 Uiso 1 1 calc R
C10 C 0.5333(6) 0.3350(18) 0.0872(3) 0.0461(17) Uani 1 1 d .
C11 C 0.5643(6) 0.5042(19) 0.1425(3) 0.0543(19) Uani 1 1 d .
C12 C 0.6773(6) 0.6157(18) 0.1784(3) 0.0516(19) Uani 1 1 d .
H12 H 0.6984 0.7255 0.2146 0.062 Uiso 1 1 calc R
C13 C 0.7533(6) 0.5587(18) 0.1588(3) 0.0524(18) Uani 1 1 d .
C14 C 0.7258(6) 0.3953(19) 0.1037(3) 0.055(2) Uani 1 1 d .
H14 H 0.7794 0.3639 0.0909 0.065 Uiso 1 1 calc R
C15 C 0.6164(5) 0.2847(19) 0.0700(3) 0.0498(18) Uani 1 1 d .
H15 H 0.5973 0.1718 0.0343 0.060 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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
C2 N1 C10 113.2(6)
C3 N2 C11 113.5(6)
O1 C1 C5 128.6(6)
O1 C1 C2 125.2(6)
C5 C1 C2 106.2(6)
N1 C2 C3 125.8(6)
N1 C2 C1 127.6(6)
C3 C2 C1 106.5(6)
N2 C3 C2 122.5(6)
N2 C3 C4 129.1(6)
C2 C3 C4 108.4(6)
C9 C4 C5 120.3(6)
C9 C4 C3 130.1(6)
C5 C4 C3 109.6(6)
C4 C5 C6 120.2(6)
C4 C5 C1 109.3(6)
C6 C5 C1 130.4(6)
C7 C6 C5 117.2(7)
C7 C6 H6 121.4
C5 C6 H6 121.4
C8 C7 C6 122.3(8)
C8 C7 H7 118.8
C6 C7 H7 118.8
C7 C8 C9 120.1(8)
C7 C8 H8 119.9
C9 C8 H8 119.9
C4 C9 C8 119.7(7)
C4 C9 H9 120.1
C8 C9 H9 120.1
N1 C10 C15 119.4(6)
N1 C10 C11 122.7(6)
C15 C10 C11 117.9(7)
N2 C11 C10 122.2(6)
N2 C11 C12 117.7(6)
C10 C11 C12 120.1(7)
C13 C12 C11 118.8(7)
C13 C12 H12 120.6
C11 C12 H12 120.6
C12 C13 C14 123.1(7)
C12 C13 Cl1 119.6(6)
C14 C13 Cl1 117.3(6)
C15 C14 C13 117.4(6)
C15 C14 H14 121.3
C13 C14 H14 121.3
C14 C15 C10 122.9(6)
C14 C15 H15 118.6
C10 C15 H15 118.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C13 1.742(7)
N1 C2 1.286(8)
N1 C10 1.353(8)
N2 C3 1.302(7)
N2 C11 1.383(8)
O1 C1 1.231(8)
C1 C5 1.471(9)
C1 C2 1.521(9)
C2 C3 1.441(9)
C3 C4 1.469(9)
C4 C9 1.361(9)
C4 C5 1.395(9)
C5 C6 1.398(9)
C6 C7 1.396(11)
C6 H6 0.9300
C7 C8 1.341(11)
C7 H7 0.9300
C8 C9 1.389(10)
C8 H8 0.9300
C9 H9 0.9300
C10 C15 1.394(8)
C10 C11 1.425(9)
C11 C12 1.426(9)
C12 C13 1.351(9)
C12 H12 0.9300
C13 C14 1.418(9)
C14 C15 1.380(8)
C14 H14 0.9300
C15 H15 0.9300
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 N1 C2 C3 0.9(10)
C10 N1 C2 C1 177.6(6)
O1 C1 C2 N1 3.1(12)
C5 C1 C2 N1 -177.4(7)
O1 C1 C2 C3 -179.7(7)
C5 C1 C2 C3 -0.2(7)
C11 N2 C3 C2 2.8(9)
C11 N2 C3 C4 -177.6(7)
N1 C2 C3 N2 -2.6(11)
C1 C2 C3 N2 -179.8(6)
N1 C2 C3 C4 177.8(7)
C1 C2 C3 C4 0.5(7)
N2 C3 C4 C9 -2.5(12)
C2 C3 C4 C9 177.2(7)
N2 C3 C4 C5 179.7(7)
C2 C3 C4 C5 -0.6(8)
C9 C4 C5 C6 2.3(11)
C3 C4 C5 C6 -179.7(6)
C9 C4 C5 C1 -177.6(6)
C3 C4 C5 C1 0.4(8)
O1 C1 C5 C4 179.3(7)
C2 C1 C5 C4 -0.1(8)
O1 C1 C5 C6 -0.5(13)
C2 C1 C5 C6 -179.9(7)
C4 C5 C6 C7 -0.8(11)
C1 C5 C6 C7 179.0(7)
C5 C6 C7 C8 0.2(12)
C6 C7 C8 C9 -1.0(13)
C5 C4 C9 C8 -3.1(11)
C3 C4 C9 C8 179.4(7)
C7 C8 C9 C4 2.5(12)
C2 N1 C10 C15 -179.8(6)
C2 N1 C10 C11 0.0(10)
C3 N2 C11 C10 -2.0(9)
C3 N2 C11 C12 178.5(6)
N1 C10 C11 N2 0.6(10)
C15 C10 C11 N2 -179.6(6)
N1 C10 C11 C12 -179.9(6)
C15 C10 C11 C12 -0.1(10)
N2 C11 C12 C13 179.7(6)
C10 C11 C12 C13 0.2(10)
C11 C12 C13 C14 0.6(11)
C11 C12 C13 Cl1 177.6(5)
C12 C13 C14 C15 -1.5(11)
Cl1 C13 C14 C15 -178.6(5)
C13 C14 C15 C10 1.6(11)
N1 C10 C15 C14 178.9(6)
C11 C10 C15 C14 -0.8(11)
