#------------------------------------------------------------------------------
#$Date: 2020-08-05 04:47:01 +0300 (Wed, 05 Aug 2020) $
#$Revision: 254819 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/09/7240983.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_7240983
loop_
_publ_author_name
'Cruz-Cabeza, A. J.'
'Taylor, E.'
'Sugden, I. J.'
'Bowskill, D. H.'
'Wright, S. E.'
'Abdullahi, H.'
'Tulegenov, D.'
'Sadiq, G.'
'Davey, R. J.'
_publ_section_title
;
 Can solvated intermediates inform us about nucleation pathways? The case
 of β-pABA
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00970A
_journal_year                    2020
_chemical_formula_moiety         'C7 H6 F N O2'
_chemical_formula_sum            'C7 H6 F N O2'
_chemical_formula_weight         155.13
_chemical_name_systematic        '4-amino-2-fluorobenzoic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-15 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.378(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.7711(8)
_cell_length_b                   3.7877(2)
_cell_length_c                   24.3334(12)
_cell_measurement_reflns_used    3882
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.6860
_cell_measurement_theta_min      2.8730
_cell_volume                     1299.28(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            7607
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.021
_diffrn_reflns_theta_min         2.890
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.30c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Water'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0558P)²+1.0215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1386
_reflns_number_total             1554
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00970a2.cif
_cod_data_source_block           c2c
_cod_database_code               7240983
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 O2(H2), N9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C11(H11)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F6 F -0.09166(5) 0.3267(2) 0.16896(3) 0.0315(2) Uani 1 1 d . . . . .
O1 O -0.13436(6) 0.8325(3) 0.01065(4) 0.0273(3) Uani 1 1 d . . . . .
O2 O -0.20337(6) 0.5639(3) 0.06950(4) 0.0290(3) Uani 1 1 d . . . . .
H2 H -0.251760 0.603261 0.042215 0.044 Uiso 1 1 d R . . . .
N9 N 0.23994(7) 0.2924(3) 0.19666(4) 0.0252(3) Uani 1 1 d . . . . .
H9A H 0.244516 0.117464 0.220398 0.030 Uiso 1 1 d R . . . .
H9B H 0.280526 0.269014 0.177508 0.030 Uiso 1 1 d R . . . .
C3 C -0.12957(8) 0.6636(3) 0.05619(5) 0.0187(3) Uani 1 1 d . . . . .
C4 C -0.03490(8) 0.5761(3) 0.09538(5) 0.0177(3) Uani 1 1 d . . . . .
C5 C -0.01812(8) 0.4090(3) 0.14855(5) 0.0199(3) Uani 1 1 d . . . . .
C7 C 0.07097(8) 0.3164(3) 0.18289(5) 0.0206(3) Uani 1 1 d . . . . .
H7 H 0.078955 0.209337 0.218417 0.025 Uiso 1 1 calc R . . . .
C8 C 0.14940(8) 0.3861(3) 0.16344(5) 0.0191(3) Uani 1 1 d . . . . .
C10 C 0.13549(8) 0.5624(3) 0.11094(5) 0.0196(3) Uani 1 1 d . . . . .
H10 H 0.187311 0.618173 0.098325 0.023 Uiso 1 1 calc R . . . .
C11 C 0.04538(8) 0.6535(3) 0.07793(5) 0.0186(3) Uani 1 1 d . . . . .
H11 H 0.037461 0.769477 0.043124 0.022 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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 H2 109.8 . . ?
H9A N9 H9B 110.5 . . ?
C8 N9 H9A 116.9 . . ?
C8 N9 H9B 114.5 . . ?
O1 C3 O2 122.77(10) . . ?
O1 C3 C4 118.34(10) . . ?
O2 C3 C4 118.89(10) . . ?
C5 C4 C3 124.96(10) . . ?
C5 C4 C11 116.30(10) . . ?
C11 C4 C3 118.70(10) . . ?
F6 C5 C4 120.21(10) . . ?
F6 C5 C7 116.32(10) . . ?
C7 C5 C4 123.46(11) . . ?
C5 C7 H7 120.5 . . ?
C5 C7 C8 118.93(11) . . ?
C8 C7 H7 120.5 . . ?
N9 C8 C7 120.38(11) . . ?
N9 C8 C10 120.45(11) . . ?
C10 C8 C7 119.14(10) . . ?
C8 C10 H10 119.9 . . ?
C11 C10 C8 120.26(10) . . ?
C11 C10 H10 119.9 . . ?
C4 C11 H11 119.1 . . ?
C10 C11 C4 121.84(11) . . ?
C10 C11 H11 119.1 . . ?
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
F6 C5 1.3587(13) . ?
O1 C3 1.2630(14) . ?
O2 H2 0.8310 . ?
O2 C3 1.2834(14) . ?
N9 H9A 0.8683 . ?
N9 H9B 0.8668 . ?
N9 C8 1.3864(15) . ?
C3 C4 1.4759(15) . ?
C4 C5 1.3945(16) . ?
C4 C11 1.4046(15) . ?
C5 C7 1.3769(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.4011(16) . ?
C8 C10 1.4013(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.3774(16) . ?
C11 H11 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F6 C5 C7 C8 178.35(10) . . . . ?
O1 C3 C4 C5 176.23(12) . . . . ?
O1 C3 C4 C11 -6.04(17) . . . . ?
O2 C3 C4 C5 -4.16(19) . . . . ?
O2 C3 C4 C11 173.57(11) . . . . ?
N9 C8 C10 C11 179.67(11) . . . . ?
C3 C4 C5 F6 -2.70(19) . . . . ?
C3 C4 C5 C7 176.89(11) . . . . ?
C3 C4 C11 C10 -176.54(11) . . . . ?
C4 C5 C7 C8 -1.25(19) . . . . ?
C5 C4 C11 C10 1.38(18) . . . . ?
C5 C7 C8 N9 -179.22(11) . . . . ?
C5 C7 C8 C10 2.92(18) . . . . ?
C7 C8 C10 C11 -2.47(18) . . . . ?
C8 C10 C11 C4 0.28(18) . . . . ?
C11 C4 C5 F6 179.52(10) . . . . ?
C11 C4 C5 C7 -0.89(19) . . . . ?
