#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:01:50 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180165 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/61/7106111.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_7106111
loop_
_publ_author_name
'Jiechao Xu'
'Jiamei Wei'
'Jiaping Zhang'
'Wenwen Zhao'
'Jie Chen'
'Hongmei Deng'
'Min Shao'
'Xiaoyu Wu'
'Hui Zhang'
'Weiguo Cao'
_publ_section_title
;
 First one-pot stereoselective synthesis of
 cis-2,3-dihydro-4-perfluoroalkyl-1H-1,5-benzodiazepines via a
 catalyst-free three-component reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              3607
_journal_paper_doi               10.1039/c0cc05039c
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C18 H13 F3 N3 O4'
_chemical_formula_weight         392.31
_chemical_name_systematic
;
?
;
_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           SHELXL-97
_cell_angle_alpha                88.156(10)
_cell_angle_beta                 70.934(9)
_cell_angle_gamma                63.004(8)
_cell_formula_units_Z            2
_cell_length_a                   8.825(6)
_cell_length_b                   9.598(7)
_cell_length_c                   12.295(9)
_cell_measurement_reflns_used    1957
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.48
_cell_measurement_theta_min      2.405
_cell_volume                     868.7(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3680
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.029(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0721
_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)+(0.1581P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2149
_refine_ls_wR_factor_ref         0.2275
_reflns_number_gt                2264
_reflns_number_total             3062
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0cc05039c.txt
_cod_data_source_block           f91211a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'TRICLINILIC' was replaced with
'triclinic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7106111
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
N2 N 0.9191(3) 0.9066(3) 0.18441(19) 0.0464(6) Uani 1 1 d . . .
N1 N 0.4995(3) 1.0558(3) 0.2877(2) 0.0511(6) Uani 1 1 d D . .
C13 C 0.7909(4) 1.0659(3) 0.2044(2) 0.0450(7) Uani 1 1 d . . .
F2 F 1.0738(3) 0.5357(2) 0.0790(2) 0.0929(8) Uani 1 1 d . . .
C14 C 0.8947(3) 0.7863(3) 0.1865(2) 0.0435(7) Uani 1 1 d . . .
C8 C 0.5997(4) 1.1357(3) 0.2532(2) 0.0448(7) Uani 1 1 d . . .
C5 C 0.2724(4) 0.9059(3) 0.3284(2) 0.0493(7) Uani 1 1 d . . .
H5 H 0.2666 0.9695 0.2696 0.059 Uiso 1 1 calc R . .
C4 C 0.4174(3) 0.8550(3) 0.3679(2) 0.0433(7) Uani 1 1 d . . .
C9 C 0.5007(4) 1.3008(3) 0.2655(3) 0.0507(7) Uani 1 1 d . . .
H9 H 0.3749 1.3487 0.2991 0.061 Uiso 1 1 calc R . .
F3 F 1.2138(3) 0.6357(3) 0.1310(3) 0.1118(10) Uani 1 1 d . . .
C3 C 0.4243(4) 0.7591(4) 0.4546(2) 0.0551(8) Uani 1 1 d . . .
H3 H 0.5216 0.7227 0.4808 0.066 Uiso 1 1 calc R . .
F1 F 1.0562(3) 0.5546(3) 0.2529(2) 0.1044(9) Uani 1 1 d . . .
C1 C 0.1485(4) 0.7691(4) 0.4610(3) 0.0582(8) Uani 1 1 d . . .
C6 C 0.1374(4) 0.8634(4) 0.3753(3) 0.0542(8) Uani 1 1 d . . .
H6 H 0.0402 0.8984 0.3490 0.065 Uiso 1 1 calc R . .
C12 C 0.8698(5) 1.1654(4) 0.1699(3) 0.0588(8) Uani 1 1 d . . .
H12 H 0.9957 1.1206 0.1388 0.071 Uiso 1 1 calc R . .
C10 C 0.5831(5) 1.3934(4) 0.2297(3) 0.0616(8) Uani 1 1 d . . .
H10 H 0.5134 1.5025 0.2387 0.074 Uiso 1 1 calc R . .
C15 C 1.0615(4) 0.6292(3) 0.1622(3) 0.0557(8) Uani 1 1 d . . .
O1 O -0.1288(4) 0.7844(4) 0.4807(3) 0.0936(10) Uani 1 1 d . . .
C11 C 0.7696(5) 1.3251(4) 0.1802(3) 0.0651(9) Uani 1 1 d . . .
H11 H 0.8264 1.3873 0.1542 0.078 Uiso 1 1 calc R . .
C2 C 0.2897(5) 0.7168(4) 0.5026(3) 0.0666(9) Uani 1 1 d . . .
H2 H 0.2938 0.6541 0.5620 0.080 Uiso 1 1 calc R . .
N3 N -0.0001(5) 0.7306(4) 0.5128(3) 0.0831(10) Uani 1 1 d . . .
C7 C 0.5698(3) 0.8966(3) 0.3182(2) 0.0441(7) Uani 1 1 d . . .
O2 O 0.0087(7) 0.6507(7) 0.5893(4) 0.178(2) Uani 1 1 d . . .
C16 C 0.7222(3) 0.7764(3) 0.2100(2) 0.0414(6) Uani 1 1 d D . .
C17 C 0.6714(4) 0.8004(3) 0.1012(2) 0.0444(7) Uani 1 1 d . . .
C18 C 0.5048(5) 0.7551(4) 0.0034(3) 0.0675(9) Uani 1 1 d . . .
H18A H 0.3987 0.8556 0.0175 0.101 Uiso 1 1 calc R . .
H18B H 0.4757 0.6724 -0.0062 0.101 Uiso 1 1 calc R . .
H18C H 0.5990 0.7500 -0.0658 0.101 Uiso 1 1 calc R . .
O3 O 0.5672(3) 0.7358(2) 0.10195(18) 0.0568(6) Uani 1 1 d . . .
O4 O 0.7209(3) 0.8662(3) 0.0260(2) 0.0680(7) Uani 1 1 d . . .
H1A H 0.385(3) 1.116(3) 0.328(2) 0.055(9) Uiso 1 1 d D . .
H16 H 0.738(4) 0.675(2) 0.234(2) 0.051(8) Uiso 1 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 '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
C14 N2 C13 128.8(2) . . ?
C8 N1 C7 124.2(2) . . ?
N2 C13 C12 112.9(3) . . ?
N2 C13 C8 129.1(2) . . ?
C12 C13 C8 118.1(3) . . ?
N2 C14 C16 129.5(2) . . ?
N2 C14 C15 116.1(2) . . ?
C16 C14 C15 114.4(2) . . ?
N1 C8 C9 116.3(2) . . ?
N1 C8 C13 125.8(2) . . ?
C9 C8 C13 117.8(2) . . ?
C6 C5 C4 120.8(3) . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 C7 118.7(2) . . ?
C5 C4 C7 122.7(2) . . ?
C10 C9 C8 122.2(3) . . ?
C2 C3 C4 121.1(3) . . ?
C6 C1 C2 121.9(3) . . ?
C6 C1 N3 118.0(3) . . ?
C2 C1 N3 120.0(3) . . ?
C1 C6 C5 118.9(3) . . ?
C11 C12 C13 122.6(3) . . ?
C9 C10 C11 119.9(3) . . ?
F3 C15 F1 106.0(3) . . ?
F3 C15 F2 107.4(3) . . ?
F1 C15 F2 105.9(3) . . ?
F3 C15 C14 114.9(2) . . ?
F1 C15 C14 111.7(3) . . ?
F2 C15 C14 110.6(3) . . ?
C12 C11 C10 119.3(3) . . ?
C3 C2 C1 118.6(3) . . ?
O2 N3 O1 122.5(4) . . ?
O2 N3 C1 117.6(4) . . ?
O1 N3 C1 119.8(4) . . ?
N1 C7 C4 110.0(2) . . ?
N1 C7 C16 110.3(2) . . ?
C4 C7 C16 111.3(2) . . ?
C14 C16 C17 109.5(2) . . ?
C14 C16 C7 110.0(2) . . ?
C17 C16 C7 113.1(2) . . ?
O4 C17 O3 124.8(3) . . ?
O4 C17 C16 124.3(3) . . ?
O3 C17 C16 110.8(2) . . ?
C17 O3 C18 116.0(2) . . ?
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
N2 C14 1.265(3) . ?
N2 C13 1.397(4) . ?
N1 C8 1.377(3) . ?
N1 C7 1.455(4) . ?
C13 C12 1.400(4) . ?
C13 C8 1.412(4) . ?
F2 C15 1.327(4) . ?
C14 C16 1.500(4) . ?
C14 C15 1.502(4) . ?
C8 C9 1.403(4) . ?
C5 C6 1.377(4) . ?
C5 C4 1.391(4) . ?
C4 C3 1.384(4) . ?
C4 C7 1.509(4) . ?
C9 C10 1.365(4) . ?
F3 C15 1.302(4) . ?
C3 C2 1.374(4) . ?
F1 C15 1.305(4) . ?
C1 C6 1.366(5) . ?
C1 C2 1.378(5) . ?
C1 N3 1.463(5) . ?
C12 C11 1.362(5) . ?
C10 C11 1.379(5) . ?
O1 N3 1.207(5) . ?
N3 O2 1.194(5) . ?
C7 C16 1.559(4) . ?
C16 C17 1.524(4) . ?
C17 O4 1.180(3) . ?
C17 O3 1.320(3) . ?
C18 O3 1.461(4) . ?
