#------------------------------------------------------------------------------
#$Date: 2015-12-09 14:42:09 +0200 (Wed, 09 Dec 2015) $
#$Revision: 171043 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/20/7222079.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_7222079
loop_
_publ_author_name
'Mir, Niyaz A.'
'Dubey, Ritesh'
'Tothadi, Srinu'
'Desiraju, Gautam R.'
_publ_section_title
;
 Combinatorial crystal synthesis of ternary solids based on
 2-methylresorcinol
;
_journal_issue                   41
_journal_name_full               CrystEngComm
_journal_page_first              7866
_journal_paper_doi               10.1039/C5CE01280E
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C22 H23 N2 O2'
_chemical_formula_weight         347.42
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-08-18 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                105.567(19)
_cell_angle_beta                 90.12(3)
_cell_angle_gamma                93.375(19)
_cell_formula_units_Z            2
_cell_length_a                   7.287(6)
_cell_length_b                   9.179(7)
_cell_length_c                   14.419(11)
_cell_measurement_temperature    150(2)
_cell_volume                     927.3(13)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_unetI/netI     0.1196
_diffrn_reflns_laue_measured_fraction_full 0.996
_diffrn_reflns_laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9785
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.571
_diffrn_reflns_theta_min         1.466
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       Block
_exptl_crystal_F_000             370
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0755
_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)+(0.1753P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1922
_refine_ls_wR_factor_ref         0.2921
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2190
_reflns_number_total             4244
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ce01280e2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7222059--7222080.cif.
;
_cod_database_code               7222079
_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_min   0.984
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.3945(3) 0.7512(2) 0.08980(15) 0.0367(5) Uani 1 1 d . .
H1 H 0.3195 0.8118 0.0801 0.055 Uiso 1 1 calc R U
N1 N 0.1338(3) 0.9151(2) 0.02399(16) 0.0282(5) Uani 1 1 d . .
O2 O 0.4962(3) 0.4270(2) 0.28660(15) 0.0342(5) Uani 1 1 d . .
H2 H 0.4504 0.3987 0.3328 0.051 Uiso 1 1 calc R U
C8 C -0.0236(4) 0.8466(3) -0.02090(18) 0.0262(6) Uani 1 1 d . .
C3 C 0.3823(4) 0.5219(3) 0.25998(19) 0.0273(6) Uani 1 1 d . .
C1 C 0.3302(4) 0.6882(3) 0.16064(18) 0.0270(6) Uani 1 1 d . .
C9 C 0.1590(4) 1.0674(3) 0.04471(18) 0.0266(6) Uani 1 1 d . .
C2 C 0.4425(4) 0.5869(3) 0.18705(18) 0.0258(6) Uani 1 1 d . .
C10 C -0.0455(4) 0.6780(3) -0.0427(2) 0.0350(7) Uani 1 1 d . .
H10A H -0.0451 0.6337 -0.1125 0.053 Uiso 1 1 calc R U
H10B H -0.1621 0.6485 -0.0170 0.053 Uiso 1 1 calc R U
H10C H 0.0565 0.6410 -0.0127 0.053 Uiso 1 1 calc R U
C6 C 0.1614(4) 0.7228(3) 0.2037(2) 0.0320(6) Uani 1 1 d . .
H6 H 0.0864 0.7913 0.1847 0.038 Uiso 1 1 calc R U
C4 C 0.2129(4) 0.5554(3) 0.3041(2) 0.0338(7) Uani 1 1 d . .
H4 H 0.1726 0.5103 0.3532 0.041 Uiso 1 1 calc R U
C5 C 0.1051(4) 0.6549(4) 0.2752(2) 0.0359(7) Uani 1 1 d . .
H5 H -0.0100 0.6774 0.3048 0.043 Uiso 1 1 calc R U
C7 C 0.6223(4) 0.5472(4) 0.1380(2) 0.0362(7) Uani 1 1 d . .
H7A H 0.6729 0.4648 0.1593 0.054 Uiso 1 1 calc R U
H7B H 0.7093 0.6363 0.1546 0.054 Uiso 1 1 calc R U
H7C H 0.6018 0.5148 0.0680 0.054 Uiso 1 1 calc R U
C11 C 0.3359(5) 1.1376(4) 0.0919(3) 0.0430(8) Uani 1 1 d . .
H11A H 0.4071 1.0596 0.1074 0.065 Uiso 1 1 calc R U
H11B H 0.3114 1.2152 0.1513 0.065 Uiso 1 1 calc R U
H11C H 0.4059 1.1842 0.0482 0.065 Uiso 1 1 calc R U
N2 N 0.3501(4) 0.2671(3) 0.40624(19) 0.0400(6) Uani 1 1 d . .
C14 C 0.2764(4) 0.0815(3) 0.5320(2) 0.0284(6) Uani 1 1 d . .
C17 C 0.2382(4) -0.0159(3) 0.5983(2) 0.0319(6) Uani 1 1 d . .
C13 C 0.2782(5) 0.0224(3) 0.4329(2) 0.0396(7) Uani 1 1 d . .
H13 H 0.2555 -0.0834 0.4055 0.047 Uiso 1 1 calc R U
C20 C 0.1702(5) -0.1991(5) 0.7241(3) 0.0586(11) Uani 1 1 d . .
H20 H 0.1471 -0.2615 0.7663 0.070 Uiso 1 1 calc R U
C15 C 0.3157(4) 0.2386(3) 0.5662(2) 0.0374(7) Uani 1 1 d . .
H15 H 0.3198 0.2861 0.6335 0.045 Uiso 1 1 calc R U
C22 C 0.2667(5) 0.0421(4) 0.6982(2) 0.0472(8) Uani 1 1 d . .
H22 H 0.3108 0.1446 0.7238 0.057 Uiso 1 1 calc R U
C16 C 0.3484(5) 0.3239(4) 0.5012(3) 0.0436(8) Uani 1 1 d . .
H16 H 0.3711 0.4303 0.5263 0.052 Uiso 1 1 calc R U
C18 C 0.1759(5) -0.1666(4) 0.5637(3) 0.0433(8) Uani 1 1 d . .
H18 H 0.1549 -0.2085 0.4965 0.052 Uiso 1 1 calc R U
C12 C 0.3131(5) 0.1170(4) 0.3735(2) 0.0449(8) Uani 1 1 d . .
H12 H 0.3106 0.0730 0.3058 0.054 Uiso 1 1 calc R U
C21 C 0.2308(6) -0.0491(5) 0.7601(3) 0.0586(11) Uani 1 1 d . .
H21 H 0.2483 -0.0077 0.8275 0.070 Uiso 1 1 calc R U
C19 C 0.1437(6) -0.2570(4) 0.6263(3) 0.0565(10) Uani 1 1 d . .
H19 H 0.1028 -0.3604 0.6010 0.068 Uiso 1 1 calc R U
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
C1 O1 H1 109.5 . .
C9 N1 C8 119.1(2) . .
C3 O2 H2 109.5 . .
N1 C8 C9 120.3(2) . 2_575
N1 C8 C10 117.3(2) . .
C9 C8 C10 122.4(3) 2_575 .
O2 C3 C4 121.9(2) . .
O2 C3 C2 117.2(2) . .
C4 C3 C2 120.9(2) . .
O1 C1 C6 121.8(2) . .
O1 C1 C2 116.5(2) . .
C6 C1 C2 121.7(2) . .
N1 C9 C8 120.6(2) . 2_575
N1 C9 C11 117.3(2) . .
C8 C9 C11 122.1(2) 2_575 .
C1 C2 C3 118.1(2) . .
C1 C2 C7 121.2(2) . .
C3 C2 C7 120.7(2) . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C5 C6 C1 118.6(3) . .
C5 C6 H6 120.7 . .
C1 C6 H6 120.7 . .
C5 C4 C3 119.2(3) . .
C5 C4 H4 120.4 . .
C3 C4 H4 120.4 . .
C4 C5 C6 121.5(3) . .
C4 C5 H5 119.3 . .
C6 C5 H5 119.3 . .
C2 C7 H7A 109.5 . .
C2 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C2 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C16 N2 C12 116.1(3) . .
C13 C14 C15 115.8(3) . .
C13 C14 C17 122.1(3) . .
C15 C14 C17 122.1(3) . .
C18 C17 C22 117.8(3) . .
C18 C17 C14 121.4(3) . .
C22 C17 C14 120.8(3) . .
C12 C13 C14 120.4(3) . .
C12 C13 H13 119.8 . .
C14 C13 H13 119.8 . .
C19 C20 C21 119.1(3) . .
C19 C20 H20 120.5 . .
C21 C20 H20 120.5 . .
C16 C15 C14 119.6(3) . .
C16 C15 H15 120.2 . .
C14 C15 H15 120.2 . .
C21 C22 C17 120.7(3) . .
C21 C22 H22 119.6 . .
C17 C22 H22 119.6 . .
N2 C16 C15 124.4(3) . .
N2 C16 H16 117.8 . .
C15 C16 H16 117.8 . .
C17 C18 C19 120.8(3) . .
C17 C18 H18 119.6 . .
C19 C18 H18 119.6 . .
N2 C12 C13 123.6(3) . .
N2 C12 H12 118.2 . .
C13 C12 H12 118.2 . .
C20 C21 C22 120.5(4) . .
C20 C21 H21 119.7 . .
C22 C21 H21 119.7 . .
C20 C19 C18 121.0(4) . .
C20 C19 H19 119.5 . .
C18 C19 H19 119.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.372(3) .
O1 H1 0.8400 .
N1 C9 1.350(3) .
N1 C8 1.350(4) .
O2 C3 1.363(3) .
O2 H2 0.8400 .
C8 C9 1.397(4) 2_575
C8 C10 1.493(4) .
C3 C4 1.402(4) .
C3 C2 1.401(4) .
C1 C6 1.394(4) .
C1 C2 1.399(4) .
C9 C8 1.397(4) 2_575
C9 C11 1.484(4) .
C2 C7 1.508(4) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C6 C5 1.391(4) .
C6 H6 0.9500 .
C4 C5 1.383(4) .
C4 H4 0.9500 .
C5 H5 0.9500 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
N2 C16 1.328(5) .
N2 C12 1.342(4) .
C14 C13 1.386(4) .
C14 C15 1.404(4) .
C14 C17 1.490(4) .
C17 C18 1.387(4) .
C17 C22 1.405(5) .
C13 C12 1.388(4) .
C13 H13 0.9500 .
C20 C19 1.377(6) .
C20 C21 1.380(6) .
C20 H20 0.9500 .
C15 C16 1.387(4) .
C15 H15 0.9500 .
C22 C21 1.393(5) .
C22 H22 0.9500 .
C16 H16 0.9500 .
C18 C19 1.392(5) .
C18 H18 0.9500 .
C12 H12 0.9500 .
C21 H21 0.9500 .
C19 H19 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N2 0.84 1.92 2.729(3) 160.1 .
O1 H1 N1 0.84 1.99 2.805(3) 164.9 .
C11 H11B O2 0.98 2.65 3.453(4) 138.9 1_565
C11 H11C O1 0.98 2.64 3.604(4) 167.6 2_675
O2 H2 N2 0.84 1.92 2.729(3) 160.1 .
O1 H1 N1 0.84 1.99 2.805(3) 164.9 .
C11 H11B O2 0.98 2.65 3.453(4) 138.9 1_565
C11 H11C O1 0.98 2.64 3.604(4) 167.6 2_675
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_4
C9 N1 C8 C9 -0.6(4) 2_575
C9 N1 C8 C10 179.8(2) .
C8 N1 C9 C8 0.6(4) 2_575
C8 N1 C9 C11 -178.5(3) .
O1 C1 C2 C3 179.2(2) .
C6 C1 C2 C3 -1.1(4) .
O1 C1 C2 C7 -1.4(4) .
C6 C1 C2 C7 178.3(3) .
O2 C3 C2 C1 -178.1(2) .
C4 C3 C2 C1 1.1(4) .
O2 C3 C2 C7 2.5(4) .
C4 C3 C2 C7 -178.3(3) .
O1 C1 C6 C5 -179.9(3) .
C2 C1 C6 C5 0.4(4) .
O2 C3 C4 C5 178.7(3) .
C2 C3 C4 C5 -0.4(4) .
C3 C4 C5 C6 -0.3(5) .
C1 C6 C5 C4 0.3(4) .
C13 C14 C17 C18 -9.8(4) .
C15 C14 C17 C18 171.3(3) .
C13 C14 C17 C22 169.5(3) .
C15 C14 C17 C22 -9.5(4) .
C15 C14 C13 C12 -1.4(5) .
C17 C14 C13 C12 179.6(3) .
C13 C14 C15 C16 1.6(4) .
C17 C14 C15 C16 -179.4(3) .
C18 C17 C22 C21 -0.8(5) .
C14 C17 C22 C21 180.0(3) .
C12 N2 C16 C15 1.6(5) .
C14 C15 C16 N2 -1.8(5) .
C22 C17 C18 C19 -0.3(5) .
C14 C17 C18 C19 178.9(3) .
C16 N2 C12 C13 -1.3(5) .
C14 C13 C12 N2 1.4(5) .
C19 C20 C21 C22 -0.7(6) .
C17 C22 C21 C20 1.3(6) .
C21 C20 C19 C18 -0.4(6) .
C17 C18 C19 C20 1.0(6) .
