#------------------------------------------------------------------------------
#$Date: 2019-11-28 21:19:47 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244652 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/93/7239324.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_7239324
loop_
_publ_author_name
'En, Da'
'Guo, Yuan'
'Chen, Bo-Ting'
'Dong, Biao'
'Peng, Meng-Jiao'
_publ_section_title
;
 Coumarin-derived Fe3+-selective fluorescent turn-off chemosensors:
 synthesis, properties, and applications in living cells
;
_journal_issue                   1
_journal_name_full               'RSC Adv.'
_journal_page_first              248
_journal_paper_doi               10.1039/C3RA44843F
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C14 H15 N O7'
_chemical_formula_weight         309.27
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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                 107.667(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0672(17)
_cell_length_b                   6.7903(8)
_cell_length_c                   13.0874(15)
_cell_measurement_reflns_used    1096
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.40
_cell_measurement_theta_min      3.32
_cell_volume                     1275.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6207
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.9743
_exptl_absorpt_correction_T_min  0.9693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0405
_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)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                1686
_reflns_number_total             2273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra44843f.txt
_cod_data_source_block           xb5923
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               7239324
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
N1 N 0.77623(12) 0.2638(3) 0.80306(14) 0.0268(4) Uani 1 1 d .
H1A H 0.7430 0.3002 0.8428 0.032 Uiso 1 1 calc R
O1 O 0.19429(10) 0.3504(3) 0.42613(12) 0.0347(4) Uani 1 1 d .
H1 H 0.1758 0.3744 0.4777 0.052 Uiso 1 1 calc R
O2 O 0.48669(10) 0.3810(2) 0.69670(11) 0.0328(4) Uani 1 1 d .
O3 O 0.61561(11) 0.3999(3) 0.82918(12) 0.0421(5) Uani 1 1 d .
O4 O 0.76940(11) 0.1690(3) 0.63505(12) 0.0390(4) Uani 1 1 d .
O5 O 0.86363(12) -0.1047(2) 0.89853(13) 0.0372(4) Uani 1 1 d .
H5 H 0.8719 -0.2170 0.8803 0.056 Uiso 1 1 calc R
O6 O 0.85395(12) 0.4809(2) 0.98500(13) 0.0384(4) Uani 1 1 d .
H6 H 0.8285 0.4736 1.0321 0.058 Uiso 1 1 calc R
O7 O 0.90360(12) 0.5718(2) 0.78882(12) 0.0362(4) Uani 1 1 d .
H7 H 0.8772 0.5919 0.7250 0.054 Uiso 1 1 calc R
C1 C 0.28866(15) 0.3272(3) 0.46030(17) 0.0281(5) Uani 1 1 d .
C2 C 0.33066(15) 0.2609(3) 0.38497(17) 0.0295(5) Uani 1 1 d .
H2 H 0.2947 0.2373 0.3146 0.035 Uiso 1 1 calc R
C3 C 0.42495(16) 0.2307(3) 0.41511(17) 0.0288(5) Uani 1 1 d .
H3 H 0.4526 0.1860 0.3648 0.035 Uiso 1 1 calc R
C4 C 0.48073(15) 0.2666(3) 0.52149(17) 0.0255(5) Uani 1 1 d .
C5 C 0.43568(15) 0.3368(3) 0.59254(16) 0.0258(5) Uani 1 1 d .
C6 C 0.34128(15) 0.3687(3) 0.56441(16) 0.0296(5) Uani 1 1 d .
H6A H 0.3136 0.4168 0.6140 0.036 Uiso 1 1 calc R
C7 C 0.57866(15) 0.2345(3) 0.56033(17) 0.0256(5) Uani 1 1 d .
H7A H 0.6094 0.1866 0.5137 0.031 Uiso 1 1 calc R
C8 C 0.62818(14) 0.2721(3) 0.66364(16) 0.0251(5) Uani 1 1 d .
C9 C 0.58096(15) 0.3522(3) 0.73621(17) 0.0282(5) Uani 1 1 d .
C10 C 0.73133(14) 0.2318(3) 0.69940(17) 0.0256(5) Uani 1 1 d .
C11 C 0.87657(14) 0.2427(3) 0.85555(16) 0.0237(5) Uani 1 1 d .
C12 C 0.90980(15) 0.0314(3) 0.84927(18) 0.0289(5) Uani 1 1 d .
H12A H 0.8983 -0.0047 0.7747 0.035 Uiso 1 1 calc R
H12B H 0.9764 0.0242 0.8845 0.035 Uiso 1 1 calc R
C13 C 0.89335(16) 0.2966(3) 0.97355(17) 0.0300(5) Uani 1 1 d .
H13A H 0.8664 0.1957 1.0075 0.036 Uiso 1 1 calc R
H13B H 0.9598 0.3003 1.0098 0.036 Uiso 1 1 calc R
C14 C 0.93423(15) 0.3730(3) 0.80364(17) 0.0299(5) Uani 1 1 d .
H14A H 0.9987 0.3707 0.8483 0.036 Uiso 1 1 calc R
H14B H 0.9317 0.3176 0.7345 0.036 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 N1 C11 126.30(18)
C9 O2 C5 123.01(16)
O1 C1 C6 121.9(2)
O1 C1 C2 117.13(19)
C6 C1 C2 120.9(2)
C3 C2 C1 119.8(2)
C2 C3 C4 120.9(2)
C5 C4 C3 116.9(2)
C5 C4 C7 118.47(19)
C3 C4 C7 124.6(2)
C6 C5 O2 116.84(18)
C6 C5 C4 123.4(2)
O2 C5 C4 119.76(18)
C5 C6 C1 118.0(2)
C8 C7 C4 121.6(2)
C7 C8 C9 119.4(2)
C7 C8 C10 118.65(19)
C9 C8 C10 121.90(19)
O3 C9 O2 114.93(18)
O3 C9 C8 127.4(2)
O2 C9 C8 117.62(18)
O4 C10 N1 123.6(2)
O4 C10 C8 120.13(19)
N1 C10 C8 116.25(18)
N1 C11 C12 111.98(17)
N1 C11 C13 106.29(16)
C12 C11 C13 108.76(17)
N1 C11 C14 112.21(17)
C12 C11 C14 106.16(17)
C13 C11 C14 111.47(17)
O5 C12 C11 111.81(16)
O6 C13 C11 111.87(17)
O7 C14 C11 113.83(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C10 1.337(3)
N1 C11 1.466(3)
O1 C1 1.364(3)
O2 C9 1.370(3)
O2 C5 1.380(2)
O3 C9 1.213(2)
O4 C10 1.230(2)
O5 C12 1.423(2)
O6 C13 1.413(3)
O7 C14 1.421(3)
C1 C6 1.382(3)
C1 C2 1.398(3)
C2 C3 1.370(3)
C3 C4 1.412(3)
C4 C5 1.391(3)
C4 C7 1.424(3)
C5 C6 1.374(3)
C7 C8 1.356(3)
C8 C9 1.454(3)
C8 C10 1.506(3)
C11 C12 1.530(3)
C11 C13 1.532(3)
C11 C14 1.536(3)
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
O1 C1 C2 C3 -178.6(2)
C6 C1 C2 C3 1.9(3)
C1 C2 C3 C4 -0.3(3)
C2 C3 C4 C5 -1.1(3)
C2 C3 C4 C7 178.3(2)
C9 O2 C5 C6 178.49(19)
C9 O2 C5 C4 -2.6(3)
C3 C4 C5 C6 1.0(3)
C7 C4 C5 C6 -178.5(2)
C3 C4 C5 O2 -177.85(18)
C7 C4 C5 O2 2.6(3)
O2 C5 C6 C1 179.45(19)
C4 C5 C6 C1 0.5(3)
O1 C1 C6 C5 178.5(2)
C2 C1 C6 C5 -2.0(3)
C5 C4 C7 C8 -0.5(3)
C3 C4 C7 C8 -180.0(2)
C4 C7 C8 C9 -1.7(3)
C4 C7 C8 C10 179.11(18)
C5 O2 C9 O3 179.48(19)
C5 O2 C9 C8 0.3(3)
C7 C8 C9 O3 -177.2(2)
C10 C8 C9 O3 1.9(4)
C7 C8 C9 O2 1.8(3)
C10 C8 C9 O2 -179.02(18)
C11 N1 C10 O4 4.1(3)
C11 N1 C10 C8 -177.45(18)
C7 C8 C10 O4 1.1(3)
C9 C8 C10 O4 -178.0(2)
C7 C8 C10 N1 -177.37(18)
C9 C8 C10 N1 3.5(3)
C10 N1 C11 C12 -61.6(3)
C10 N1 C11 C13 179.75(18)
C10 N1 C11 C14 57.7(3)
N1 C11 C12 O5 -59.3(2)
C13 C11 C12 O5 57.9(2)
C14 C11 C12 O5 177.95(17)
N1 C11 C13 O6 -52.0(2)
C12 C11 C13 O6 -172.75(17)
C14 C11 C13 O6 70.5(2)
N1 C11 C14 O7 49.0(2)
C12 C11 C14 O7 171.63(17)
C13 C11 C14 O7 -70.1(2)
