#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:45:17 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180275 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/61/7116176.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_7116176
loop_
_publ_author_name
'Cagide, F.'
'Silva, T.'
'Reis, J.'
'Gaspar, A.'
'Borges, F.'
'Gomes, L. R.'
'Low, J. N.'
_publ_section_title
;
 Discovery of two new classes of potent monoamine oxidase-B inhibitors by
 tricky chemistry.
;
_journal_issue                   14
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2832
_journal_paper_doi               10.1039/c4cc08798d
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C16 H11 N O3'
_chemical_formula_sum            'C16 H11 N O3'
_chemical_formula_weight         265.26
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-12-16 deposited with the CCDC.
2014-12-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.306(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6795(2)
_cell_length_b                   7.3003(3)
_cell_length_c                   24.6020(17)
_cell_measurement_reflns_used    13855
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1196.27(10)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_molecular_graphics    'PLATON (Spek,2009)'
_computing_publication_material
;
Oscail (McArdle et al., 2004),
SHELXS-97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
Oscail (McArdle et al., 2004),
SHELXS-97 (Sheldrick, 2008)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
    Number of images: 212
               Slice: -32.0000 - 74.0000
         Image width: 0.5000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 72.0000
                 Phi: -150.0000
                 XTD: 44.9816
              2theta: -15.9849
scan:
    Number of images: 181
               Slice: -68.5000 - 22.0000
         Image width: 0.5000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: 90.0000
                 XTD: 44.9816
              2theta: -15.9849
scan:
    Number of images: 184
               Slice: -69.0000 - 23.0000
         Image width: 0.5000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: -90.0000
                 XTD: 44.9816
              2theta: -15.9849
scan:
    Number of images: 144
               Slice: -82.0000 - -10.0000
         Image width: 0.5000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: -90.0000
                 XTD: 44.9816
              2theta: -15.9849
scan:
    Number of images: 30
               Slice: 3.0000 - 18.0000
         Image width: 0.5000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: -60.0000
                 XTD: 44.9816
              2theta: -15.9849
scan:
    Number of images: 236
               Slice: -44.0000 - 74.0000
         Image width: 0.5000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 72.0000
                 Phi: 30.0000
                 XTD: 44.9816
              2theta: -15.9849
scan:
    Number of images: 137
               Slice: -97.0000 - -28.5000
         Image width: 0.5000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -36.0000
                 Phi: -90.0000
                 XTD: 44.9816
              2theta: -15.9849

;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support MiTeGen
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.138828
_diffrn_orient_matrix_UB_12      -0.053577
_diffrn_orient_matrix_UB_13      0.017913
_diffrn_orient_matrix_UB_21      0.042864
_diffrn_orient_matrix_UB_22      -0.123928
_diffrn_orient_matrix_UB_23      -0.038465
_diffrn_orient_matrix_UB_31      0.005636
_diffrn_orient_matrix_UB_32      -0.010154
_diffrn_orient_matrix_UB_33      0.038994
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15473
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_transf_matrix_11  -0.138828
_diffrn_reflns_transf_matrix_12  -0.053577
_diffrn_reflns_transf_matrix_13  0.017913
_diffrn_reflns_transf_matrix_21  0.042864
_diffrn_reflns_transf_matrix_22  -0.123928
_diffrn_reflns_transf_matrix_23  -0.038465
_diffrn_reflns_transf_matrix_31  0.005636
_diffrn_reflns_transf_matrix_32  -0.010154
_diffrn_reflns_transf_matrix_33  0.038994
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 3.1 b18 (Rigaku, 20112)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0473P)²+0.4205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0953
_reflns_number_gt                2464
_reflns_number_total             2728
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc08798d2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7116175--7116176.cif.'
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7116176
#BEGIN Tags that were not found in dictionaries:
_publcif_datablock.id            {fffe6069-cc8d-46bd-bfd2-5e38eb240432}
#END Tags that were not found in dictionaries
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_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
O1 O 0.96968(10) 0.16970(11) 0.46208(3) 0.01970(18) Uani 1 1 d .
C2 C 0.95768(15) 0.26453(15) 0.50834(4) 0.0180(2) Uani 1 1 d .
H2 H 1.0803 0.3003 0.5275 0.022 Uiso 1 1 calc R
O3 O 0.98085(11) 0.44831(13) 0.60415(3) 0.0289(2) Uani 1 1 d .
N3 N 0.63925(12) 0.45520(12) 0.60561(3) 0.01538(19) Uani 1 1 d .
H3 H 0.5282 0.4248 0.5862 0.018 Uiso 1 1 calc R
C3 C 0.78555(14) 0.31362(14) 0.53004(4) 0.0150(2) Uani 1 1 d .
O4 O 0.42775(10) 0.30536(10) 0.51855(3) 0.01618(17) Uani 1 1 d .
C4 C 0.59241(14) 0.26473(13) 0.50195(4) 0.0137(2) Uani 1 1 d .
C5 C 0.43566(15) 0.09938(14) 0.42032(4) 0.0159(2) Uani 1 1 d .
H5 H 0.3063 0.1285 0.4315 0.019 Uiso 1 1 calc R
C6 C 0.45339(16) -0.00193(14) 0.37365(4) 0.0184(2) Uani 1 1 d .
H6 H 0.3364 -0.0424 0.3527 0.022 Uiso 1 1 calc R
C7 C 0.64363(17) -0.04529(15) 0.35709(4) 0.0212(2) Uani 1 1 d .
H7 H 0.6547 -0.1160 0.3250 0.025 Uiso 1 1 calc R
C8 C 0.81501(17) 0.01319(16) 0.38666(4) 0.0213(2) Uani 1 1 d .
H8 H 0.9441 -0.0157 0.3753 0.026 Uiso 1 1 calc R
C8A C 0.79424(15) 0.11569(14) 0.43361(4) 0.0167(2) Uani 1 1 d .
C311 C 0.61349(15) 0.54109(13) 0.65591(4) 0.0154(2) Uani 1 1 d .
C312 C 0.76868(15) 0.62605(14) 0.68775(4) 0.0175(2) Uani 1 1 d .
H312 H 0.9014 0.6266 0.6763 0.021 Uiso 1 1 calc R
C313 C 0.72697(16) 0.70976(15) 0.73638(4) 0.0199(2) Uani 1 1 d .
H313 H 0.8324 0.7677 0.7580 0.024 Uiso 1 1 calc R
C314 C 0.53409(17) 0.71032(16) 0.75387(4) 0.0219(2) Uani 1 1 d .
H314 H 0.5076 0.7669 0.7874 0.026 Uiso 1 1 calc R
C315 C 0.38016(17) 0.62679(16) 0.72164(4) 0.0219(2) Uani 1 1 d .
H315 H 0.2475 0.6272 0.7331 0.026 Uiso 1 1 calc R
C316 C 0.41876(16) 0.54285(15) 0.67292(4) 0.0182(2) Uani 1 1 d .
H316 H 0.3126 0.4865 0.6511 0.022 Uiso 1 1 calc R
C4A C 0.60762(15) 0.15983(14) 0.45147(4) 0.0145(2) Uani 1 1 d .
C31 C 0.81252(15) 0.41354(14) 0.58339(4) 0.0168(2) Uani 1 1 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 O1 C8A 118.51(8)
O1 C2 C3 125.41(9)
O1 C2 H2 117.3
C3 C2 H2 117.3
C31 N3 C311 128.32(9)
C31 N3 H3 115.8
C311 N3 H3 115.8
C2 C3 C4 119.69(9)
C2 C3 C31 115.12(9)
C4 C3 C31 125.18(9)
O4 C4 C3 124.07(9)
O4 C4 C4A 121.56(9)
C3 C4 C4A 114.36(9)
C6 C5 C4A 120.38(9)
C6 C5 H5 119.8
C4A C5 H5 119.8
C5 C6 C7 120.04(10)
C5 C6 H6 120.0
C7 C6 H6 120.0
C8 C7 C6 120.86(10)
C8 C7 H7 119.6
C6 C7 H7 119.6
C7 C8 C8A 118.31(10)
C7 C8 H8 120.8
C8A C8 H8 120.8
O1 C8A C4A 121.45(9)
O1 C8A C8 116.24(9)
C4A C8A C8 122.31(10)
C316 C311 C312 119.78(9)
C316 C311 N3 116.44(9)
C312 C311 N3 123.75(9)
C313 C312 C311 119.32(10)
C313 C312 H312 120.3
C311 C312 H312 120.3
C314 C313 C312 121.24(10)
C314 C313 H313 119.4
C312 C313 H313 119.4
C313 C314 C315 119.03(10)
C313 C314 H314 120.5
C315 C314 H314 120.5
C316 C315 C314 120.57(10)
C316 C315 H315 119.7
C314 C315 H315 119.7
C315 C316 C311 120.06(10)
C315 C316 H316 120.0
C311 C316 H316 120.0
C8A C4A C5 118.10(9)
C8A C4A C4 120.57(9)
C5 C4A C4 121.33(9)
O3 C31 N3 124.85(10)
O3 C31 C3 120.74(9)
N3 C31 C3 114.39(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3395(13)
O1 C8A 1.3770(12)
C2 C3 1.3519(14)
C2 H2 0.9500
O3 C31 1.2261(13)
N3 C31 1.3512(13)
N3 C311 1.4093(13)
N3 H3 0.8800
C3 C4 1.4613(13)
C3 C31 1.5005(14)
O4 C4 1.2377(12)
C4 C4A 1.4691(14)
C5 C6 1.3782(14)
C5 C4A 1.4033(14)
C5 H5 0.9500
C6 C7 1.3996(15)
C6 H6 0.9500
C7 C8 1.3773(16)
C7 H7 0.9500
C8 C8A 1.3919(14)
C8 H8 0.9500
C8A C4A 1.3904(14)
C311 C316 1.3960(14)
C311 C312 1.3968(14)
C312 C313 1.3901(15)
C312 H312 0.9500
C313 C314 1.3887(16)
C313 H313 0.9500
C314 C315 1.3911(15)
C314 H314 0.9500
C315 C316 1.3875(15)
C315 H315 0.9500
C316 H316 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O4 0.88 1.95 2.7064(11) 143 .
C2 H2 O3 0.95 2.31 2.7065(13) 104 .
C312 H312 O3 0.95 2.30 2.8914(13) 120 .
C2 H2 O4 0.95 2.35 3.1452(13) 141 1_655
C5 H5 O1 0.95 2.44 3.3893(13) 174 1_455
C316 H316 O3 0.95 2.44 3.3394(13) 159 1_455
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
C8A O1 C2 C3 -0.19(16)
O1 C2 C3 C4 -0.90(16)
O1 C2 C3 C31 177.81(9)
C2 C3 C4 O4 -179.32(10)
C31 C3 C4 O4 2.11(16)
C2 C3 C4 C4A 1.16(14)
C31 C3 C4 C4A -177.41(9)
C4A C5 C6 C7 0.06(15)
C5 C6 C7 C8 -0.48(16)
C6 C7 C8 C8A 0.34(17)
C2 O1 C8A C4A 0.95(15)
C2 O1 C8A C8 -178.27(9)
C7 C8 C8A O1 179.44(9)
C7 C8 C8A C4A 0.22(16)
C31 N3 C311 C316 -170.52(10)
C31 N3 C311 C312 11.18(16)
C316 C311 C312 C313 0.66(15)
N3 C311 C312 C313 178.90(9)
C311 C312 C313 C314 0.06(16)
C312 C313 C314 C315 -0.63(16)
C313 C314 C315 C316 0.49(17)
C314 C315 C316 C311 0.21(16)
C312 C311 C316 C315 -0.79(15)
N3 C311 C316 C315 -179.17(9)
O1 C8A C4A C5 -179.80(9)
C8 C8A C4A C5 -0.63(15)
O1 C8A C4A C4 -0.60(15)
C8 C8A C4A C4 178.58(9)
C6 C5 C4A C8A 0.48(15)
C6 C5 C4A C4 -178.72(9)
O4 C4 C4A C8A -179.98(9)
C3 C4 C4A C8A -0.45(14)
O4 C4 C4A C5 -0.80(15)
C3 C4 C4A C5 178.73(9)
C311 N3 C31 O3 -1.28(18)
C311 N3 C31 C3 177.24(9)
C2 C3 C31 O3 1.09(15)
C4 C3 C31 O3 179.72(10)
C2 C3 C31 N3 -177.50(9)
C4 C3 C31 N3 1.13(15)
#BEGIN Loops that were not found in dictionaries:
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
#END Loops that were not found in dictionaries
