#------------------------------------------------------------------------------
#$Date: 2017-10-13 13:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201982 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/18/4111832.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_4111832
loop_
_publ_author_name
'Archan Dey'
'Michael T. Kirchner'
'Venu R. Vangala'
'Gautam R. Desiraju'
'Raju Mondal'
'Judith A. K. Howard'
_publ_contact_author_address
;
School of Chemistry
University of Hyderabad
Hyderabad 500 046
India
;
_publ_contact_author_email       desiraju@uohyd.ernet.in
_publ_contact_author_fax         '91 40 23010567'
_publ_contact_author_name        'Professor Gautam R. Desiraju'
_publ_contact_author_phone       '91 40 23134828'
_publ_section_title
;
 Crystal Structure Prediction of Aminols: Advantages of a Supramolecular
 Synthon Approach with Experimental Structures
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10545
_journal_page_last               10559
_journal_paper_doi               10.1021/ja042738c
_journal_volume                  127
_journal_year                    2005
_chemical_formula_moiety         'C7 H9 N O'
_chemical_formula_sum            'C7 H9 N O'
_chemical_formula_weight         123.15
_chemical_melting_point          424
_chemical_name_common            2A3MP
_chemical_name_systematic        2-Amino-3-methylphenol
_space_group_IT_number           45
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'I 2 -2c'
_symmetry_space_group_name_H-M   'I b a 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.6090(7)
_cell_length_b                   7.4822(2)
_cell_length_c                   8.2703(3)
_cell_measurement_reflns_used    4528
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.475
_cell_measurement_theta_min      2.881
_cell_volume                     1337.17(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'smart 1k CCD area detector'
_diffrn_measurement_method       'omega 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  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6130
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       Cube
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1541
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0330
_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)+(0.0452P)²+0.4347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0882
_reflns_number_gt                1479
_reflns_number_total             1541
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja042738csi20050407_114233_02.cif
_cod_data_source_block           2a
_cod_database_code               4111832
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, 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
O1 O 0.24487(5) 0.24680(15) 0.04976(13) 0.0294(2) Uani 1 1 d
N1 N 0.20478(6) 0.05980(17) -0.20344(16) 0.0302(3) Uani 1 1 d
C2 C 0.16250(6) 0.17676(16) -0.12372(15) 0.0222(3) Uani 1 1 d
C4 C 0.06312(6) 0.31720(18) -0.09673(17) 0.0264(3) Uani 1 1 d
C6 C 0.14522(6) 0.39502(17) 0.08911(17) 0.0261(3) Uani 1 1 d
C5 C 0.08446(6) 0.41362(19) 0.03607(18) 0.0280(3) Uani 1 1 d
C1 C 0.18452(6) 0.27650(16) 0.00872(15) 0.0219(3) Uani 1 1 d
C3 C 0.10193(7) 0.19927(17) -0.17928(16) 0.0238(3) Uani 1 1 d
C7 C 0.08016(9) 0.0990(2) -0.3277(2) 0.0371(4) Uani 1 1 d
H6 H 0.1619(8) 0.457(2) 0.178(2) 0.027(4) Uiso 1 1 d
H112 H 0.1850(10) -0.034(3) -0.256(3) 0.052(6) Uiso 1 1 d
H5 H 0.0583(8) 0.493(3) 0.096(2) 0.035(5) Uiso 1 1 d
H7C H 0.0794(10) -0.032(3) -0.313(3) 0.053(6) Uiso 1 1 d
H4 H 0.0208(8) 0.333(2) -0.1381(19) 0.028(4) Uiso 1 1 d
H111 H 0.2322(10) 0.022(3) -0.135(3) 0.043(5) Uiso 1 1 d
H7B H 0.0382(9) 0.139(3) -0.356(2) 0.030(4) Uiso 1 1 d
H7A H 0.1081(10) 0.130(3) -0.426(3) 0.050(6) Uiso 1 1 d
H1 H 0.2567(10) 0.317(3) 0.126(3) 0.043(6) Uiso 1 1 d
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
O1 0.0246(5) 0.0318(5) 0.0316(5) -0.0006(4) -0.0021(4) 0.0047(4)
N1 0.0366(7) 0.0291(6) 0.0251(5) -0.0009(5) 0.0034(5) 0.0122(5)
C2 0.0280(6) 0.0184(5) 0.0203(5) 0.0028(5) 0.0062(5) 0.0025(5)
C4 0.0241(6) 0.0252(7) 0.0299(7) 0.0003(5) 0.0008(5) 0.0002(5)
C6 0.0293(7) 0.0237(6) 0.0253(6) -0.0024(5) -0.0001(5) 0.0008(5)
C5 0.0269(7) 0.0265(6) 0.0307(7) -0.0033(5) 0.0039(6) 0.0049(5)
C1 0.0228(6) 0.0204(6) 0.0227(6) 0.0051(5) 0.0031(5) 0.0006(4)
C3 0.0284(7) 0.0192(6) 0.0239(6) 0.0014(5) 0.0013(5) 0.0003(5)
C7 0.0428(9) 0.0317(8) 0.0369(9) -0.0110(6) -0.0094(7) 0.0029(7)
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
C1 O1 H1 111.6(15)
C2 N1 H112 112.7(13)
C2 N1 H111 109.5(14)
H112 N1 H111 112(2)
C3 C2 C1 120.56(11)
C3 C2 N1 121.45(12)
C1 C2 N1 117.91(12)
C5 C4 C3 120.95(13)
C5 C4 H4 121.2(10)
C3 C4 H4 117.8(10)
C5 C6 C1 119.17(12)
C5 C6 H6 123.9(10)
C1 C6 H6 117.0(10)
C6 C5 C4 120.62(12)
C6 C5 H5 117.1(11)
C4 C5 H5 122.2(11)
O1 C1 C6 124.46(12)
O1 C1 C2 115.45(11)
C6 C1 C2 120.09(12)
C4 C3 C2 118.57(12)
C4 C3 C7 121.55(13)
C2 C3 C7 119.88(12)
C3 C7 H7C 113.5(15)
C3 C7 H7B 109.4(11)
H7C C7 H7B 108.3(17)
C3 C7 H7A 110.0(12)
H7C C7 H7A 109.0(19)
H7B C7 H7A 106.4(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3657(17)
O1 H1 0.86(3)
N1 C2 1.4266(16)
N1 H112 0.93(2)
N1 H111 0.87(2)
C2 C3 1.3973(19)
C2 C1 1.4082(18)
C4 C5 1.393(2)
C4 C3 1.3957(19)
C4 H4 0.984(17)
C6 C5 1.3912(19)
C6 C1 1.3963(18)
C6 H6 0.943(19)
C5 H5 0.96(2)
C3 C7 1.514(2)
C7 H7C 0.99(2)
C7 H7B 0.98(2)
C7 H7A 1.04(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2282663
