#------------------------------------------------------------------------------
#$Date: 2017-10-13 13:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201982 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/23/4102327.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_4102327
loop_
_publ_author_name
'Panče Naumov'
'Janusz Kowalik'
'Kyril M. Solntsev'
'Anthony Baldridge'
'Jong-Seok Moon'
'Christine Kranz'
'Laren M. Tolbert'
_publ_section_title
;
 Topochemistry and Photomechanical Effects in Crystals of Green
 Fluorescent Protein-like Chromophores: Effects of Hydrogen Bonding and
 Crystal Packing
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5845
_journal_page_last               5857
_journal_paper_doi               10.1021/ja100844m
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C12 H11 F N2 O'
_chemical_formula_sum            'C12 H11 F N2 O'
_chemical_formula_weight         218.23
_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                 105.1860(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.12770(10)
_cell_length_b                   11.2873(2)
_cell_length_c                   13.6337(2)
_cell_measurement_reflns_used    6195
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.83
_cell_measurement_theta_min      2.38
_cell_volume                     1058.56(3)
_computing_cell_refinement       'APEX2 software (Bruker, 2007)'
_computing_data_collection       'APEX2 software (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2005)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker SMART APEX2 diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multilayer confocal TXS mirror'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15287
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       columnar
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0519
_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)+(0.0858P)²+0.2113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1637
_reflns_number_gt                2012
_reflns_number_total             2466
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja100844m_si_004.cif
_cod_data_source_block           t3_1
_cod_database_code               4102327
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
F1 F 0.2546(3) 0.19120(13) 0.48356(12) 0.0925(6) Uani 1 1 d .
O1 O 0.1474(3) 0.53757(16) 0.25452(12) 0.0698(5) Uani 1 1 d .
N10 N 0.1714(3) 0.71227(15) 0.34443(13) 0.0534(4) Uani 1 1 d .
N12 N 0.2458(3) 0.64829(16) 0.50538(13) 0.0554(4) Uani 1 1 d .
C2 C 0.2931(4) 0.2550(2) 0.56969(18) 0.0598(6) Uani 1 1 d .
C3 C 0.3361(4) 0.1940(2) 0.6611(2) 0.0754(7) Uani 1 1 d .
H3 H 0.3382 0.1116 0.6622 0.090 Uiso 1 1 calc R
C4 C 0.3751(5) 0.2568(3) 0.7487(2) 0.0760(8) Uani 1 1 d .
H4 H 0.4043 0.2168 0.8105 0.091 Uiso 1 1 calc R
C5 C 0.3724(4) 0.3810(3) 0.74798(19) 0.0723(6) Uani 1 1 d .
H5 H 0.4006 0.4239 0.8083 0.087 Uiso 1 1 calc R
C6 C 0.3264(4) 0.4381(2) 0.65467(17) 0.0604(5) Uani 1 1 d .
H6 H 0.3226 0.5205 0.6535 0.072 Uiso 1 1 calc R
C1 C 0.2862(3) 0.37818(18) 0.56401(15) 0.0480(4) Uani 1 1 d .
C7 C 0.2389(3) 0.43420(17) 0.46444(15) 0.0486(5) Uani 1 1 d .
H7 H 0.2163 0.3825 0.4095 0.058 Uiso 1 1 calc R
C8 C 0.2232(3) 0.55031(18) 0.44033(15) 0.0480(4) Uani 1 1 d .
C9 C 0.1750(4) 0.59137(19) 0.33385(16) 0.0514(5) Uani 1 1 d .
C11 C 0.2125(4) 0.7402(2) 0.44552(17) 0.0548(5) Uani 1 1 d .
C13 C 0.1276(5) 0.7916(3) 0.2572(2) 0.0757(7) Uani 1 1 d .
H13C H 0.0547 0.7497 0.1983 0.113 Uiso 1 1 calc R
H13B H 0.2467 0.8201 0.2454 0.113 Uiso 1 1 calc R
H13A H 0.0525 0.8575 0.2705 0.113 Uiso 1 1 calc R
C14 C 0.2196(5) 0.8645(2) 0.4809(2) 0.0818(9) Uani 1 1 d .
H14A H 0.2249 0.8659 0.5520 0.123 Uiso 1 1 calc R
H14C H 0.1054 0.9057 0.4434 0.123 Uiso 1 1 calc R
H14B H 0.3331 0.9026 0.4703 0.123 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.1471(17) 0.0424(7) 0.0843(10) -0.0054(7) 0.0234(13) 0.0005(11)
O1 0.0935(12) 0.0630(10) 0.0506(8) -0.0030(8) 0.0146(9) 0.0024(10)
N10 0.0599(11) 0.0442(9) 0.0552(10) 0.0089(7) 0.0133(9) 0.0049(9)
N12 0.0663(11) 0.0469(9) 0.0511(9) 0.0002(8) 0.0121(9) 0.0020(11)
C2 0.0684(15) 0.0466(12) 0.0659(13) 0.0054(10) 0.0204(13) 0.0021(12)
C3 0.0804(18) 0.0567(14) 0.0916(18) 0.0315(14) 0.0272(17) 0.0097(15)
C4 0.0729(17) 0.0879(19) 0.0702(16) 0.0347(15) 0.0242(15) 0.0104(16)
C5 0.0847(17) 0.0770(16) 0.0547(12) 0.0148(12) 0.0173(14) 0.0080(16)
C6 0.0739(15) 0.0531(12) 0.0537(12) 0.0052(10) 0.0159(13) 0.0049(13)
C1 0.0467(10) 0.0429(10) 0.0560(11) 0.0079(8) 0.0161(9) 0.0039(10)
C7 0.0555(12) 0.0420(10) 0.0468(10) -0.0049(8) 0.0108(10) 0.0003(10)
C8 0.0491(11) 0.0440(10) 0.0498(10) 0.0011(8) 0.0111(10) 0.0004(10)
C9 0.0544(12) 0.0475(11) 0.0526(11) 0.0009(9) 0.0142(11) 0.0015(10)
C11 0.0578(13) 0.0417(11) 0.0641(12) 0.0012(10) 0.0144(12) -0.0003(11)
C13 0.0792(17) 0.0715(16) 0.0768(16) 0.0321(13) 0.0213(16) 0.0148(16)
C14 0.108(2) 0.0456(13) 0.0873(18) -0.0090(13) 0.0178(18) 0.0006(16)
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
C11 N10 C9 109.28(17)
C11 N10 C13 128.6(2)
C9 N10 C13 122.1(2)
C11 N12 C8 105.11(17)
F1 C2 C3 117.8(2)
F1 C2 C1 119.4(2)
C3 C2 C1 122.8(2)
C4 C3 C2 118.7(2)
C3 C4 C5 121.2(2)
C6 C5 C4 118.1(3)
C1 C6 C5 122.7(2)
C6 C1 C2 116.5(2)
C6 C1 C7 124.67(19)
C2 C1 C7 118.8(2)
C8 C7 C1 129.34(19)
C7 C8 N12 128.66(18)
C7 C8 C9 121.86(19)
N12 C8 C9 109.47(17)
O1 C9 N10 126.1(2)
O1 C9 C8 131.5(2)
N10 C9 C8 102.39(19)
N12 C11 N10 113.74(19)
N12 C11 C14 124.4(2)
N10 C11 C14 121.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.343(3)
O1 C9 1.211(3)
N10 C11 1.369(3)
N10 C9 1.373(3)
N10 C13 1.456(3)
N12 C11 1.303(3)
N12 C8 1.400(3)
C2 C3 1.386(3)
C2 C1 1.393(3)
C3 C4 1.354(4)
C4 C5 1.402(4)
C5 C6 1.387(3)
C6 C1 1.372(3)
C1 C7 1.455(3)
C7 C8 1.349(3)
C8 C9 1.476(3)
C11 C14 1.480(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660102
