#------------------------------------------------------------------------------
#$Date: 2024-07-05 18:36:19 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292984 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/87/7248705.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_7248705
loop_
_publ_author_name
'Li, Zhonghua'
'Jia, Shengzhe'
'Wu, Songgu'
'Gong, Junbo'
_publ_section_title
;
 Influence of the substituent in the benzene ring on the structure and
 properties of two isostructural crystals
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              3021
_journal_page_last               3025
_journal_paper_doi               10.1039/D4CE00163J
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C9 H11 N O3'
_chemical_formula_sum            'C9 H11 N O3'
_chemical_formula_weight         181.19
_chemical_name_systematic        Methyl-2-amino-5-methoxybenzoate
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-10-31 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   29.7023(15)
_cell_length_b                   29.7023(15)
_cell_length_c                   5.3577(3)
_cell_measurement_reflns_used    3791
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.2450
_cell_measurement_theta_min      2.3540
_cell_volume                     4093.4(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    8.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  30.00   1.00    8.00    --  -30.00  45.00  90.00  150
  3  ω   -120.00   0.00   1.00    8.00    --  -30.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0226147000
_diffrn_orient_matrix_UB_12      -0.0023626000
_diffrn_orient_matrix_UB_13      0.0037293000
_diffrn_orient_matrix_UB_21      0.0157496000
_diffrn_orient_matrix_UB_22      0.0274499000
_diffrn_orient_matrix_UB_23      -0.0048791000
_diffrn_orient_matrix_UB_31      -0.0000273000
_diffrn_orient_matrix_UB_32      0.0010892000
_diffrn_orient_matrix_UB_33      0.1322252000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10582
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         2.375
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       needle
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0474P)²+2.3370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1432
_reflns_number_total             1865
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00163j2.cif
_cod_data_source_block           r20211103d
_cod_depositor_comments
'Adding full bibliography for 7248705--7248706.cif.'
_cod_original_cell_volume        4093.4(5)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7248705
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C9H11NO3
_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.
;
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.978
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C6(H6)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.699
_oxdiff_exptl_absorpt_empirical_full_min 0.769
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
O3 O 0.46756(5) 0.77306(4) 0.9622(2) 0.0369(3) Uani 1 1 d . . . . .
O1 O 0.62746(4) 0.90135(4) 0.1784(2) 0.0347(3) Uani 1 1 d . . . . .
O2 O 0.59043(4) 0.81603(4) 0.2539(2) 0.0315(3) Uani 1 1 d . . . . .
N1 N 0.60014(6) 0.95803(6) 0.4743(3) 0.0397(4) Uani 1 1 d . . . . .
C9 C 0.46169(7) 0.72481(6) 0.8800(4) 0.0392(5) Uani 1 1 d . . . . .
H9A H 0.448413 0.717936 0.708549 0.059 Uiso 1 1 calc GR . . . .
H9B H 0.437163 0.696825 0.989498 0.059 Uiso 1 1 calc GR . . . .
H9C H 0.495470 0.726464 0.885358 0.059 Uiso 1 1 calc GR . . . .
C5 C 0.50201(6) 0.81648(6) 0.8296(3) 0.0280(4) Uani 1 1 d . . . . .
C4 C 0.50656(6) 0.86335(6) 0.9124(3) 0.0306(4) Uani 1 1 d . . . . .
H4 H 0.486932 0.863322 1.052497 0.037 Uiso 1 1 calc R . . . .
C3 C 0.53881(6) 0.90892(6) 0.7942(3) 0.0304(4) Uani 1 1 d . . . . .
H3 H 0.541005 0.940119 0.853244 0.036 Uiso 1 1 calc R . . . .
C2 C 0.56904(6) 0.91114(6) 0.5866(3) 0.0281(4) Uani 1 1 d . . . . .
C1 C 0.56474(6) 0.86387(6) 0.5050(3) 0.0252(4) Uani 1 1 d . . . . .
C6 C 0.53048(6) 0.81686(6) 0.6279(3) 0.0263(4) Uani 1 1 d . . . . .
H6 H 0.527166 0.785124 0.569798 0.032 Uiso 1 1 calc R . . . .
C7 C 0.59689(6) 0.86353(6) 0.2987(3) 0.0264(4) Uani 1 1 d . . . . .
C8 C 0.62153(7) 0.81335(7) 0.0549(3) 0.0350(4) Uani 1 1 d . . . . .
H8A H 0.613531 0.825214 -0.100783 0.053 Uiso 1 1 calc GR . . . .
H8B H 0.613793 0.777373 0.035198 0.053 Uiso 1 1 calc GR . . . .
H8C H 0.658443 0.835642 0.094868 0.053 Uiso 1 1 calc GR . . . .
H1A H 0.6029(8) 0.9856(8) 0.544(4) 0.051(6) Uiso 1 1 d . . . . .
H1B H 0.6202(8) 0.9600(8) 0.345(4) 0.057(7) Uiso 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 C9 116.28(13) . . ?
C7 O2 C8 115.52(13) . . ?
C2 N1 H1A 118.1(14) . . ?
C2 N1 H1B 119.7(14) . . ?
H1A N1 H1B 122(2) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C5 C4 115.12(14) . . ?
C6 C5 O3 125.58(14) . . ?
C6 C5 C4 119.29(15) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.70(15) . . ?
C3 C4 H4 119.7 . . ?
C4 C3 H3 119.1 . . ?
C4 C3 C2 121.89(15) . . ?
C2 C3 H3 119.1 . . ?
N1 C2 C3 119.00(15) . . ?
N1 C2 C1 123.71(16) . . ?
C3 C2 C1 117.28(14) . . ?
C2 C1 C7 120.33(14) . . ?
C6 C1 C2 119.98(14) . . ?
C6 C1 C7 119.65(14) . . ?
C5 C6 C1 120.84(14) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 O2 121.48(14) . . ?
O1 C7 C1 125.55(15) . . ?
O2 C7 C1 112.95(13) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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
O3 C9 1.424(2) . ?
O3 C5 1.3766(19) . ?
O1 C7 1.2173(18) . ?
O2 C7 1.3470(19) . ?
O2 C8 1.4385(19) . ?
N1 C2 1.367(2) . ?
N1 H1A 0.87(2) . ?
N1 H1B 0.89(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C5 C4 1.402(2) . ?
C5 C6 1.369(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.362(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.410(2) . ?
C2 C1 1.414(2) . ?
C1 C6 1.414(2) . ?
C1 C7 1.464(2) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
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
O3 C5 C4 C3 -179.00(15) . . . . ?
O3 C5 C6 C1 179.83(14) . . . . ?
N1 C2 C1 C6 -178.20(15) . . . . ?
N1 C2 C1 C7 3.8(2) . . . . ?
C9 O3 C5 C4 179.23(15) . . . . ?
C9 O3 C5 C6 0.2(2) . . . . ?
C5 C4 C3 C2 -0.4(3) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C4 C3 C2 N1 179.16(16) . . . . ?
C4 C3 C2 C1 -0.1(2) . . . . ?
C3 C2 C1 C6 1.1(2) . . . . ?
C3 C2 C1 C7 -176.90(14) . . . . ?
C2 C1 C6 C5 -1.4(2) . . . . ?
C2 C1 C7 O1 -2.5(2) . . . . ?
C2 C1 C7 O2 176.20(13) . . . . ?
C6 C5 C4 C3 0.1(2) . . . . ?
C6 C1 C7 O1 179.54(15) . . . . ?
C6 C1 C7 O2 -1.8(2) . . . . ?
C7 C1 C6 C5 176.54(15) . . . . ?
C8 O2 C7 O1 -0.5(2) . . . . ?
C8 O2 C7 C1 -179.27(13) . . . . ?
